Total synthesis of (+)-quassin

Citation
Tkm. Shing et Q. Jiang, Total synthesis of (+)-quassin, J ORG CHEM, 65(21), 2000, pp. 7059-7069
Citations number
49
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
21
Year of publication
2000
Pages
7059 - 7069
Database
ISI
SICI code
0022-3263(20001020)65:21<7059:TSO(>2.0.ZU;2-X
Abstract
A total synthesis of (+)-quassin from naturally occurring (S)-(+)-carvone i s described. The total number of steps was 28, and the overall yield was ab out 2.6%. The synthetic strategy for the construction of the tetracyclic ca rbon framework was based on a C-->ABC-->ABCD ring annulation sequence, invo lving an aldol reaction, an intramolecular Diels-Alder reaction, and an int ramolecular acylation as the key steps. Subsequent functionalization of rin g A and ring C then afforded the target (+)-quassin.