Total synthesis of (+)-quassin

T. K.M. Shing; Q. Jiang

doi:10.1021/jo000877g

Total synthesis of (+)-quassin

T. K.M. Shing, Q. Jiang

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	7059-7069
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	65
Issue number	21
DOIs	https://doi.org/10.1021/jo000877g
Publication status	Published - 2000 Oct 20

ASJC Scopus subject areas

Organic Chemistry

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AU - Jiang, Q.

PY - 2000/10/20

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AB - 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.

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Total synthesis of (+)-quassin

Abstract

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