A Synthesis of (+)‐Oblongolide

Tony Kung Ming Shing, Jun Yang

Research output: Contribution to journalArticle

Abstract

The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)‐3a,5a,6,7,8,9,9a,9b‐octahydro‐7,9b‐dimethylnaphtho[1,2‐c]furan‐1(3H)‐one 2 by a 7‐stage synthesis of its enantiomer 1 from (+)‐citronellol involving a regioselective reduction and an intramolecular Diels‐Alder reaction (IMDA) as the key steps. (+)‐Citronellol was converted into methyl (2E,4E,10E)‐(S)‐(+)‐11‐tert‐butoxycarbonyl‐7‐methyl‐undeca‐2,4,10‐trienoate 7 by sequential Lemieux‐Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth‐Emmons‐Homer alkenation. A regioselective reduction of the methoxycarbonyl group in 7 afforded tert‐butyl (2.E,8E,10E)‐(S)‐(+)‐2,6‐dimethyl‐12‐hydroxy‐dodeca‐2,8,10‐trienoate 8 from which (+)‐oblongolide was readily obtained via an IMDA reaction.

Original languageEnglish
Pages (from-to)709-712
Number of pages4
JournalJournal of the Chinese Chemical Society
Volume42
Issue number4
DOIs
Publication statusPublished - 1995 Jan 1
Externally publishedYes

Keywords

  • Absolute configuration
  • Citronellol
  • Intramolecular Diels‐Alder reaction
  • Oblongolide

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'A Synthesis of (+)‐Oblongolide'. Together they form a unique fingerprint.

  • Cite this