Total synthesis of (+)-quassin

T. K.M. Shing, Q. Jiang

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

A total synthesis of (+)-quassin from naturally occurring (S)-(+)-carvone is described. The total number of steps was 28, and the overall yield was about 2.6%. The synthetic strategy for the construction of the tetracyclic carbon framework was based on a C→ABC→ABCD ring annulation sequence, involving an aldol reaction, an intramolecular Diels-Alder reaction, and an intramolecular acylation as the key steps. Subsequent functionalization of ring A and ring C then afforded the target (+)-quassin.

Original languageEnglish
Pages (from-to)7059-7069
Number of pages11
JournalJournal of Organic Chemistry
Volume65
Issue number21
DOIs
Publication statusPublished - 2000 Oct 20

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this