Asymmetric total synthesis of (+)-dihydroitomanallene B and formal synthesis of (?)-kumausallene?

Chemical Communications Pub Date: 2022-09-27 DOI: 10.1039/D2CC04574E

Abstract

The first asymmetric total synthesis of (+)-dihydroitomanallene B and its two diastereomers, and the formal synthesis of (?)-kumausallene are reported. The synthesis of the former was completed in 18 steps from 1,4-butanediol (3.4% overall yield), with diastereoselective Tsuji–Trost cyclization to access cis-2,5-disubstituted-3-oxygenated THF scaffold and a Corey–White–Posner reaction to install the bromoallene moiety as the key steps. In addition, the enantioselective formal total synthesis of (?)-kumausallene involving the key Tsuji–Trost cyclization is also realized.

Graphical abstract: Asymmetric total synthesis of (+)-dihydroitomanallene B and formal synthesis of (?)-kumausallene
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