Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Alexander M. Sherwood, Samuel E. Williamson, Stephanie N. Johnson, Anil Yilmaz, Victor W. Day, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.

Original languageEnglish
Pages (from-to)980-992
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number2
DOIs
StatePublished - Jan 19 2018

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

  • Organic Chemistry

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