C
Christopher D. Vanderwal
Researcher at University of California, Irvine
Publications - 114
Citations - 3192
Christopher D. Vanderwal is an academic researcher from University of California, Irvine. The author has contributed to research in topics: Chemistry & Ring (chemistry). The author has an hindex of 32, co-authored 106 publications receiving 2798 citations. Previous affiliations of Christopher D. Vanderwal include University of California, Berkeley & University of California, Los Angeles.
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Journal ArticleDOI
Stereoselective Halogenation in Natural Product Synthesis
TL;DR: This Review critically discusses the methods and strategies used for stereoselective introduction of halogen atoms in the context of natural product synthesis, as well as existing methods that have not yet seen application in complex molecule synthesis.
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Site-Selective Aliphatic C–H Chlorination Using N-Chloroamides Enables a Synthesis of Chlorolissoclimide
Ryan K. Quinn,Zef A. Könst,Sharon E. Michalak,Yvonne Schmidt,Anne R. Szklarski,Alex Flores,Sangkil Nam,David Horne,Christopher D. Vanderwal,Erik J. Alexanian +9 more
TL;DR: A site-selective chlorination of aliphatic C-H bonds using readily available N-chloroamides is reported and this transformation is applied to a synthesis of chlorolissoclimide, a potently cytotoxic labdane diterpenoid that preliminary assays indicate are moderately active against aggressive melanoma and prostate cancer cell lines.
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Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites
Rubén M. Buey,Enrique Calvo,Isabel Barasoain,Oriol Pineda,Michael C. Edler,Ruth Matesanz,Gemma Cerezo,Christopher D. Vanderwal,Billy W. Day,Erik J. Sorensen,Juan Antonio López,José Manuel Andreu,Ernest Hamel,J. Fernando Díaz +13 more
TL;DR: The pore region of beta-tubulin is an undescribed binding site that elucidates the mechanism by which taxoid-site compounds reach the kinetically unfavorable lumenal site and explains how taxoids-site drugs induce microtubule formation from dimeric and oligomeric tubulin.
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Enantioselective formal hydration of alpha,beta-unsaturated imides by Al-catalyzed conjugate addition of oxime nucleophiles.
TL;DR: Application of the (salen)Al-catalyzed asymmetric conjugate addition of salicylaldoxime to α,β-unsaturated imides revealed a high level of catalyst-induced diastereoselectivity, underscoring its potential utility for polyketide natural product synthesis.
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An enantioselective synthesis of FR182877 provides a chemical rationalization of its structure and affords multigram quantities of its direct precursor.
TL;DR: The evolution of a strategy culminating in an efficient, enantioselective synthesis of the potent microtubule-stabilizing agent FR182877 is described, which creates a complex pentacycle from a 19-membered macrocyclic pentaene, forming seven new stereogenic centers in a fully diastereocontrolled fashion.