Total synthesis of (+)-4-Oxo-5,6,9,10-tetradehydro-4,5-secofuranoeremophilane-5,1-carbolactone via Novel Lactone Construction through Aliene Intramolecular Cycloaddition

Kenji Hayakawa, Fumi Nagatsugi, Ken Kanematsu

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

The first asymmetric synthesis of the title compound 1 is described. The crucial step is a facile construction of the tricyclic lactone, the basic skeleton of 1, via aliene intramolecular cycloaddition. Methyl (R)-(-)-3-hydroxyhept-6-enoate (3) was converted into the (R)-propargyl ether 8 in six steps. Base treatment (t-BuOK/t-BuOH, 83°C) of 8 caused a smooth cyclization via the intramolecular Diels-Alder reaction of the allenyl ether intermediate to give 9, which on successive hydration and oxidation provided the lactone 10 as a mixture of diastereomers. Aromatization of 10 afforded a single product (11), which was subjected to the Wacker oxidation to give (R)-(+)-1.

Original languageEnglish
Pages (from-to)860-863
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number4
DOIs
Publication statusPublished - 1988 Feb 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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