About

Clayton H. Heathcock, born in 1936, is a Professor Emeritus in the Department of Chemistry at the University of California, Berkeley. He holds a B.Sc. from Abilene Christian College, Texas (1958), and a Ph.D. in Organic Chemistry from the University of Colorado (1963). His postdoctoral work was conducted at Columbia University, and he has been recognized with numerous fellowships and awards, including the Alfred P. Sloan Foundation Fellowship, Alexander von Humboldt Senior Scientist, and Miller Research Professor at UC Berkeley. Heathcock has served as chairman of the Division of Organic Chemistry of the American Chemical Society, and has held leadership roles such as editor-in-chief of Organic Syntheses and the Journal of Organic Chemistry. His research focuses on organic synthesis, particularly the utilization of laboratory skill to construct complex structures through multistep synthesis. He has a long-standing fascination with organic reactions, aiming to understand their mechanisms and apply them to the synthesis of intricate natural products with unusual biological activity. His work emphasizes the importance of mechanistic reasoning and creative synthesis design to advance the science of large-molecule synthesis, contributing to the understanding of complex chemical structures and their synthesis.

Research topics

• Chemistry
• Stereochemistry
• Computer science
• Organic chemistry
• Information retrieval

Selected publications

• 2.08 The Aldol Reaction: Group I and Group II Enolates

  Elsevier eBooks · 2014-01-01 · 8 citations

  book-chapter1st authorCorresponding
  PublisherDOI

• Synthesis and biological evaluation of analogs of altohyrtin C (spongistatin 2)

  Tetrahedron · 2007-11-10 · 9 citations

  articleSenior author
  PublisherDOI

• Synthesis of Tricolorin F (I).

  ChemInform · 2004-10-29

  articleSenior author
  PublisherDOI

• Synthesis of Tricolorin F

  The Journal of Organic Chemistry · 2004-01-06 · 33 citations

  articleSenior author

  A hetero-trisaccharide resin glycoside of jalapinolic acid known as tricolorin F has been synthesized. The approach involved the preparation of intermediate 5 and a subsequent coupling reaction with imidate 6 to produce disaccharide 7, which after deacetylation generated intermediate 8. A further coupling between this glycosyl acceptor and the quinovose glycosyl donor 9 resulted in the formation of the tricoloric acid C derivative 10. Basic hydrolysis afforded the intermediate 11, which was subsequently lactonized under Yamaguchi conditions to produce protected macrolactone 12. Removal of acetonide and benzyl protecting groups afforded pure tricolorin F (1).

  PublisherDOI

• Total synthesis of (±)-halichlorine, (±)-pinnaic acid, and (±)-tauropinnaic acid

  Proceedings of the National Academy of Sciences · 2004-08-06 · 55 citations

  articleOpen accessSenior authorCorresponding

  The related marine natural products halichlorine, pinnaic acid, and tauropinnaic acid have been synthesized. The described route provided access to all three compounds from a common, late-stage intermediate. The synthesis began with 1-pyrrolidino-1-cyclopentene from which an intermediate possessing the three contiguous stereocenters of the natural products was synthesized in just four steps. Olefin cross metathesis followed by a hydrogenation/hydrogenolysis reaction stereoselectively formed the piperidine ring. Use of a beta-lactam group provided internal protection for the highly congested nitrogen atom during side-chain elaboration. The beta-lactam was subsequently reduced directly to an amino aldehyde, which after the Horner-Wadsworth-Emmons reaction was elaborated to pinnaic acid. The same amino aldehyde was also transformed into halichlorine after a thiol-mediated cyclization sequence to form the dehydroquinolizidine ring system.

  PublisherOA PDFDOI

• Henry Rapoport

  The Journal of Organic Chemistry · 2003-01-01

  editorial1st authorCorresponding

  ADVERTISEMENT RETURN TO ISSUEEditorialNEXTHenry RapoportClayton H. HeathcockView Author Information October 20, 2002Cite this: J. Org. Chem. 2003, 68, 1, 1–2Publication Date (Web):January 3, 2003Publication History Published online3 January 2003Published inissue 1 January 2003https://pubs.acs.org/doi/10.1021/jo023590nhttps://doi.org/10.1021/jo023590neditorialACS PublicationsCopyright © 2003 American Chemical Society. This publication is available under these Terms of Use. Request reuse permissions This publication is free to access through this site. Learn MoreArticle Views979Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail PDF (69 KB) Get e-AlertscloseSUBJECTS:Biosynthesis,Medicinal chemistry,Organic chemistry,Pharmaceuticals,Students Get e-Alerts

  PublisherDOI

• A Second-Generation Synthesis of the C1−C28 Portion of the Altohyrtins (Spongistatins)

  Journal of the American Chemical Society · 2003-09-27 · 62 citations

  articleSenior author

  A practical second-generation synthesis of an advanced intermediate in our total synthesis of altohyrtin C (spongistatin 2) has been developed. A new approach to the C1-C15 (AB) portion features a vinyllithium addition to an aldehyde followed by a palladium-catalyzed allylic reduction to install the troublesome C13-C15 segment. Our general approach to the C16-C28 (CD) spiroketal has been retained, but some improvements have been made. Most notably, the kinetically controlled CD-spiroketalization reaction now proceeds in high yield with excellent diastereoselection. This new strategy uses the anti-aldol coupling used in our first-generation synthesis to join AB and CD fragments. A total of 9.6 g of intermediate 57 has been produced using this improved route.

  PublisherDOI

• (2 <i>SR</i> ,3 <i>SR</i> )‐2,4‐Dimethyl‐3‐hydroxypentanoic Acid

  Organic Syntheses · 2003-04-28 · 9 citations

  otherSenior author

  Abstract (2 SR ,3 SR )‐2,4‐Dimethyl‐3‐hydroxypentanoic acid intermediate: 2,6‐dimethylphenyl propanoate intermediate: 2′,6′‐Dimethylphenyl (2 SR ,3 SR )‐2,4‐dimethyl‐3‐hydroxypentanoate. product: (2 SR ,3 SR )‐2,4‐dimethyl‐3‐hydroxypentanoic acid

  PublisherDOI

• Methyl ( <i>trans</i> ‐2‐Iodo‐1‐Tetralin)Carbamate

  Organic Syntheses · 2003-04-28

  other1st authorCorresponding

  Abstract Methyl ( trans ‐2‐Iodo‐1‐Tetralin)Carbamate product: methyl ( trans ‐2‐iodo‐1‐tetralin)carbamate

  PublisherDOI

• 2‐Methyl‐2‐(Trimethylsiloxy)Pentan‐3‐one

  Organic Syntheses · 2003-04-28 · 1 citations

  otherSenior author

  Abstract 2‐Methyl‐2‐(trimethylsiloxy)pentan‐3‐one intermediate: 2‐hydroxybutanenitrile intermediate: 2‐[(1′‐ethoxy)‐1‐ethoxy]butanenitrile intermediate: 2‐hydroxy‐2‐methylpentan‐3‐one product: 2‐methyl‐2‐(trimethylsiloxy)pentan‐3‐one

  PublisherDOI

Recent grants

• NIH Grant R01AI015027

  NIH · $1.4M · 2003

• NIH Grant R37AI015027

  NIH · $2.3M · 1998

Frequent coauthors

• Robin D. Clark

  Loma Linda University

  26 shared

• Michael C. Pirrung

  University of California, Riverside

  21 shared

• Bruce G. Szczepankiewicz

  GlaxoSmithKline (United States)

  20 shared

• Terry Rosen

  18 shared

• Robert G. Bergman

  Lawrence Berkeley National Laboratory

  17 shared

• C. C. Cheng

  National Kaohsiung University of Science and Technology

  16 shared

• D. F. Liu

  University of California, Berkeley

  16 shared

• Yan-Xiang Luo

  Ningbo University

  16 shared

Awards & honors

• Ernest Guenther Award (ACS) (1986)
• ACS Award for Creative Work in Organic Synthesis (1990)
• A.C. Cope Scholar (1990)
• Prelog Medal, ETH (1991)
• American Academy of Arts and Sciences (1991)