News
Spring 2025
(1) Congratulations to Dr. Andrea Bucknam for successfully defending her doctoral thesis in May, and a sincere thanks to Prof. Mingji Dai (Emory University) for serving on Andrea’s thesis committee!
(2) We are settling into our new laboratory space located in the Falling Leaves Foundation Medical Innovation Building at UCI… Pictures will be posted soon!
(3) We welcome Dr. Ibrahim Celik as a new member of the lab!
Winter 2025
The Micalizio laboratory has relocated to the University of California, Irvine! We are entering an exciting time for research in the group as we position our laboratory in an environment where our advances in organic synthesis will “grow” in an environment that welcomes natural product-inspired drug discovery and development. The laboratory will be one of five that will occupy the recently created Robert A. Mah Molecular Innovation Center located within the new Falling Leaves Medical Innovation Building. Also, Andrea and Josh’s manuscript describing the discovery of a potent and selective ER-b agonist that has dual activity as an antagonist of AR was recently accepted for publication in ACS Med. Chem. Lett.! Here, one of our recently reported asymmetric synthesis pathways to “steroidal” systems took center stage as a central driver of the scientific discovery.
Fall 2024
Best wishes to Zachary Stempel as he transitions to AstraZeneca! Congratulations!
Summer 2024
(1) Congratulations to Joshua Nicholson for successfully defending his Ph.D. thesis! – Well done Dr. Nicholson!!
(2) Great news for Andrea Bucknam!… She has recently been awarded a National Institutes of Health predoctoral fellowship!
(3) Zac Stempel has successfully defended his Ph.D. thesis! Well done Dr. Stempel…!
(4) Congratulations to Joshua Nicholson!… his manuscript describing the design and discovery of ent-estranes as modulators of the glucocorticoid receptor that inhibit release of the pro-inflammatory cytokines TNF-a and IL-6 was accepted for publication in J. Med. Chem.!
Spring 2024
Spring 2024: Well deserved congratulations to Zachary Stempel for leading an effort to access 26-norlupeol and 26-norgermanicol that resulted in the identification of a novel natural product-inspired antagonist of the androgen receptor! Also, congratulations to our collaborators Prof. Christopher Coss and Hanna Radomska from College of Pharmacy at The Ohio State University. The manuscript describing this effort was recently accepted for publication in Org. Lett.!
Winter 2024
After a long and winding road of unanticipated challenges, we are proud to announce that Dr. Tim Fazekas has established an asymmetric de novo means of establishing a highly functionalized intact limonoid system. His manuscript describing this accomplishment was just accepted for publication in Org. Lett.! Congratulations, Tim!
Congratulations to Lauren and our team of collaborators including Thomas Koelblen (UF-Pharmacy), Harry Chobanian (ROME Therapeutics), Ariele Viacava Follis (ROME Therapeutics), and Thomas Burris (UF-Pharmacy) on the their manuscript entitled “From Functional Fatty Acids to Potent and Selective Natural Product-Inspired Mimetics via Conformational Profiling” that was recently accepted for publication in ACS Central Science!
Fall 2023
Congratulations to newly minted Dr. Lauren Markham!… She recently defended her PhD thesis and will be moving on to a position at Choate, Hall and Stewart, LLP in Boston! We thank Professor John L. Wood (Baylor University) for serving as an “external” member of Lauren’s thesis committee!
Summer 2023
Congratulations to Joshua Nicholson! His manuscript that describes the first asymmetric de novo total syntheses of the fundamental tetracyclic triterpenoids, euphol and tirucallol, has been accepted for publication in Organic Letters!
Spring 2023
Congratulations to Andrea Bucknam! Her manuscript describing a counter biomimetic lanostane-to-cucurbitane type transformation has recently been accepted for publication in a special virtual issue of Tetrahedron that honors Professor John L. Wood!
Fall 2022
Congratulations to HtooTint Wai! Her synthetic pathway to lanostanes has recently been published in The Journal of Organic Chemistry!
Summer 2022
Congratulations to Adam Millham! His manuscript that describes a unique syn-SN2′ addition reaction to steroidal C14–C17 vinylepoxides and establishes a conceptually unique and highly stereoselective means of installing C17 substituents onto steroidal systems has been accepted for publication in Organic Letters!
Spring 2022
Htoo Tint Wai’s manuscript focused on efforts directed toward the asymmetric de novo synthesis of euphanes has been accepted for publication in Organic Letters! Congratulations to HtooTint and our collaborators at the University of Florida (Thomas Koelblen, Matthew E. Hayes and Thomas P. Burris)!
Andrea Buckram’s manuscript describing the first total synthesis of a cucurbitane natural product has been accepted for publication in the Journal of the American Chemical Society! Congratulations!
Winter 2022
Congratulations to Joshua Nicholson, Adam Millham, Andrea Bucknam, Lauren Markham and Xenia Sailors! Their manuscript, “A General Enantioselective Divergent Four-Stage Approach to Fused Tetracyclic Terpenoid Systems” has been accepted for publication in The Journal of Organic Chemistry. The article discusses solutions to problems associated with stereoselective formation of the “steroidal” C9–C10 bond, and reports highly selective means to establish a C9 quaternary center (syn- or anti- with respect to the pre-existing quaternary center at C13). In addition, subsequent oxidative rearrangement reactions are shown to be feasible with either stereoisomer and compatible with a variety of C9 substituents.
Summer 2021
Congratulations to Lauren Markham and Jessica Tolbert (Kull Laboratory)! Their manuscript describing the design, synthesis, and discovery of a chiral hydrindane mimetic of palmitoleic acid as a potent inhibitor of ToxT was accepted for publication in ACS Medicinal Chemistry Letters! Overall, the chiral conformation that palmitoleic acid adopts when bound to ToxT was used as inspiration for the design of a conformationally constrained mimic based on a chiral hydrindane carbocyclic core. This pursuit was enabled/driven by the application of our alkoxide-directed metallacycle-mediated annulative cross-coupling chemistry.
Winter 2021
Congratulations to Zac Shalit, Lucas Valdes, and Wan Shin Kim! They manuscript that describes a de novo asymmetric synthesis of a rare marine-derived pregnene was recently accepted for publication in Organic Letters! The approach taken demonstrates a means to convert an unnatural enantiomer of an estrane system to a natural enantiomer of an androstane system, and finally to the natural product. Overall, this work demonstrates one of the several means by which our annulative coupling technology can be leveraged to access natural products.
Summer 2020
Congratulations to Adam Millham and Chinmay Bhatt on their new manuscript that was recently accepted for publication in Organic Letters! It describes varying the stereochemical course of a cyclization reaction central to our strategy for the synthesis of tetracyclic terpenoids.
Spring 2020
We welcome Andrea Bucknam (from the College of the Holy Cross) and Xenia Sailors (from USF) as new members of our group!
Congratulations to the ryanodol team (Kang Du, Matthew Kier and Zachary Stempel)! They completed a synthesis of anhydroryanodol featuring one of our new alkyne–diketone annulation reactions! While also constituting a formal total synthesis of ryanodol, this marks the first successful application of one of these metallacycle-centered annulation reactions in natural product synthesis. Their manuscript has been accepted as a Communication in the Journal of the American Chemical Society!
Fall 2019
We welcome Joshua Nicholson as a new member of our group! He comes to us from the College of the Holy Cross.
Summer 2019
Congratulations to Dr. Wan Shin Kim! He has just accepted a position as a PhD chemist at Boehringer Ingelheim!
Congratulations to Rajdip Karmakar – his studies focused on developing a general metallacycle-mediated annulation reaction for the stereoselective synthesis of a wide variety of fused carbocycles has been accepted for publication in Organic Letters!
We welcome Lauren Markham as a new member of our group! She comes to us from Baylor University where she performed undergraduate research with Prof. John Wood.
Spring 2019
Congratulations to Wan Shin Kim for successfully defending his PhD thesis! He is the first PhD student to complete studies at Dartmouth College – well done!
Congratulations to Wan Shin and Zac, along with our collaborators from the Gaur and Burris laboratories (Sidney Nguyen and Emmalie Schoepke)! Their manuscript describing a new asymmetric strategy for the synthesis of tetracyclic terpenoids and the discovery of a potent and selective agonist of the estrogen receptor beta that has potent anti-glioblastoma properties, has been accepted for publication in Nature Communications! Also see Dartmouth’s press release on this advance (also: AAAS EurekAlert). By mid July of 2019 this article has received an Altmetric score of 58, placing it “in the top 5% of all research outputs ever tracked by Altmetric”!
Congratulations to Bobby and our collaborators from the Gaur laboratory (Divya, Jennifer, and Carmen)! Their manuscript describing the asymmetric synthesis of desmethylene corialactone D and the discovery of natural product-inspired inhibitors of NGF-promoted neurite outgrowth has been accepted for publication in Organic Letters!
Winter 2019
Congratulations to Adam, Matt, Bobby, Rajdip, and Zac on the acceptance of their manuscript describing a complementary process to Pauson–Khand-like annulation reactions for the synthesis of fully substituted cyclopentenones in Organic Letters!
Fall 2018
Kang and Matt’s manuscript concerning an approach to the synthesis of a ryanoid tetracycle has been designated an “ACS Editor’s Choice” article. Well done!
Congratulations to Kang and Matt on the acceptance of their manuscript describing efforts toward the total synthesis of ryanodol in Organic Letters!
Congratulations to HtooTint, Kang, Jason, and Wan Shin on the acceptance of their manuscript describing the synthesis and discovery of a novel bioactive steroid in Organic Letters!
Summer 2018
Best wishes to Dr. Natasha O’Rourke as she heads off to begin her career at Takeda Pharmaceuticals!
The group welcomes two new graduate students – Zachary Stempel and Chinmay Bhatt!
Winter 2018
Congratulations to Zach Shalit! His first manuscript has been accepted for publication in a special issue of Arkivoc in honor of our colleague Professor Gordon Gribble!
Fall 2017
Warm wishes sent along with Professor Haruki Mizoguchi as he begins his academic career at Okayama University!
We congratulate Professor Amos Smith on his recent total synthesis of (–)-nahuoic acid Ci(Bii) – an accomplishment that features late stage application of one of our metallacycle-mediated cross-coupling reactions!
Dr. Haruki Mizoguchi has just accepted a position as an Assistant Professor at Okayama University with Professor Akira Sakakura! We look forward to seeing Professor Mizoguchi thrive in his new academic position!
– Natasha’s communication regarding function-oriented studies of pectenotoxin 2 (PTX2) was just accepted for publication in Organic Letters and was selected as an ACS Editors’ Choice!
We are happy to welcome Adam Millham as a first-year graduate student in our group!
Summer 2017
Congratulations to Matt, Bobby and Natasha! Their manuscript that describes a new stereoselective annulation reaction for the synthesis of densely functionalized 5- and 6-membered rings has been accepted for publication as a Communication in the Journal of the American Chemical Society!
We welcome two new group members – postdoctoral associate Dr. Rajdip Karmakar (PhD mentor: Prof. Daesung Lee), and Ms. Htoo Tint Wai (first year graduate student).
Spring 2017
Congratulations to Wan Shin and Kang! Their manuscript that describes a concise enantiospecific synthesis of partially aromatic steroids using a metallacycle-mediated annulative cross-coupling reaction has been accepted for publication in Nature Chemistry (DOI: 10.1038/NCHEM.2865)!
We are happy to welcome Mr. Jason Anesini from Binghamton U. as a visiting undergraduate researcher for the Summer of 2017, and Zachary Shalit as a new graduate student!
Congratulations to Xiayun! Her manuscript on the application of metallacycle-mediated cross-coupling to the synthesis of neurotrophic seco-prezizaane natural products has been accepted for publication in Strategies and Tactics in Organic Chemistry.
Congratulations to Haruki! His manuscript describing the development of metallacycle-mediated annulative cross-coupling has been accepted for publication in a special issue of the Isr. J. Chem. in honor of Professors Stuart L. Schreiber and K. C. Nicolaou.
Fall 2016
We welcome the addition of Dr. Kang Du to the Micalizio Group! Kang received his Ph.D. from Shanghai Institute of Organic Chemistry where he studied in the laboratory of Professor Wenjun Tang.
Summer 2016
Congratulations to Haruki – his manuscript describing a new convergent synthesis of angularly substituted trans-fused decalins was recently accepted for publication by Angewandte Chemie!
Congratulations to Haruki – his review of metallacycle-mediated annulative cross-coupling chemistry has been accepted for publication in Isr. J. Chem.
Congratulation to Natasha and Matt – their review on the use of metallacycle-mediated cross-coupling in natural product synthesis has been accepted for publication as a Report in Tetrahedron!
We are happy to welcome Bobby Leon as a new graduate student in the lab! He’s off to a great start, working on a new stereoselective metallacycle-mediated cross-coupling reaction!
Congratulations to Claudio – he has accepted a position as a PhD chemist at DiCE Molecules!
Congratulations to James and Haruki – their manuscript focused on accelerating the rate of metallacycle-mediated reductive cross-coupling between internal alkynes has been accepted for publication in Tetrahedron Letters!
Spring 2016
Congratulation to Claudio – his manuscript focused on the development of a synthetic route to the pentacyclic core of the cortistatins has been accepted for publication in Organic Letters!
Congratulations to David – he has accepted an offer to attend Harvard Medical School !!
Congratulations to Cannon – he will be pursuing a summer internship as an undergraduate at Merck Research Laboratories in Rahway, NJ !
Winter 2016
Welcome new graduate students: Jonathan Iaconelli and James Cassidy
Congratulations to Natasha – her manuscript describing metallacycle-mediated cross-coupling between cyclopropenes was accepted for publication in Organic Letters!
Congratulations to Xiayun – her manuscript describing the total syntheses of several seco-prezizaane sesquiterpenes has been published in the Journal of the American Chemical Society!
Congratulations to Xiayun – she recently accepted a position at Pfizer Inc.!
Fall 2015
Congratulations to Haruki – his manuscript describing a convergent annulation process for the assembly of densely functionalized decalins was accepted for publication in the Journal of the American Chemical Society!
Spring 2015
Congratulations to Valer – he recently accepted a position at GlaxoSmithKline!
