Total synthesis of (+)-quassin

Tony Kung Ming Shing, Q. Jiang

Research output: Contribution to journalArticle

29 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
Externally publishedYes

Fingerprint

Acylation
Carbon
quassin
carvone
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of (+)-quassin. / Shing, Tony Kung Ming; Jiang, Q.

In: Journal of Organic Chemistry, Vol. 65, No. 21, 20.10.2000, p. 7059-7069.

Research output: Contribution to journalArticle

Shing, TKM & Jiang, Q 2000, 'Total synthesis of (+)-quassin', Journal of Organic Chemistry, vol. 65, no. 21, pp. 7059-7069. https://doi.org/10.1021/jo000877g
Shing, Tony Kung Ming ; Jiang, Q. / Total synthesis of (+)-quassin. In: Journal of Organic Chemistry. 2000 ; Vol. 65, No. 21. pp. 7059-7069.
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