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


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Sherwood A. M. , Williamson S. E. , Johnson S. N. , Yilmaz A., Day V. W. , Prisinzano T. E.

JOURNAL OF ORGANIC CHEMISTRY, vol.83, no.2, pp.980-992, 2018 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 83 Issue: 2
  • Publication Date: 2018
  • Doi Number: 10.1021/acs.joc.7b02324
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.980-992

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.