Total synthesis of (+)-quassin |
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Authors: | Shing T K Jiang Q |
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Institution: | Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong. tonyshing@cuhk.edu.hk |
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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. |
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