Issue 12, 2018

Total synthesis of (−)-akaol A via a conformational constraint strategy

Abstract

The enantioselective total synthesis of (−)-akaol A has been achieved. The key reaction features a well-designed Friedel–Crafts cyclization, which ensured a cis-fused B/C ring through a conformational constraint strategy. In marked control to trans-fused B/C ring cyclization promoted by a routine acid, the complete cis selective formation of the B/C ring was realized for the first time. Bistri-fluoromethane-sulfonimide promoted the key cyclization effectively. Our synthesis involves 13 steps from known aldehyde 2 and proceeds in 10.7% overall yield.

Graphical abstract: Total synthesis of (−)-akaol A via a conformational constraint strategy

Supplementary files

Article information

Article type
Research Article
Submitted
11 Apr 2018
Accepted
27 Apr 2018
First published
28 Apr 2018

Org. Chem. Front., 2018,5, 1886-1889

Total synthesis of (−)-akaol A via a conformational constraint strategy

H. Liu, D. Chen, W. Xu, L. Dang and H. Qin, Org. Chem. Front., 2018, 5, 1886 DOI: 10.1039/C8QO00375K

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