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Stereodiverse Iterative Synthesis of 1,3-Polyol Arrays through Asymmetric Catalytic Hydrogenation. Formal Total Synthesis of (−)-Cyanolide A

Author:
Che, Wen, Li, Yu-Zhen, Liu, Jin-Chi, Zhu, Shou-Fei, Xie, Jian-Hua, Zhou, Qi-Lin
Source:
Organic letters 2019 v.21 no.7 pp. 2369-2373
ISSN:
1523-7052
Subject:
catalysts, chemical structure, diastereoselectivity, enantioselectivity, esters, hydrogenation, hydrolysis, polyketides, protocols
Abstract:
An iterative protocol was developed for highly diastereo- and enantioselective construction of high-order 1,3-polyols via iridium-catalyzed asymmetric hydrogenation of β-alkyl-β-keto esters. The protocol involves four operations—asymmetric hydrogenation, hydroxy protection, ester hydrolysis, and C-acylation—and the catalyst loading can be as low as 0.005 mol %. The configurations of all stereogenic centers of 1,3-polyols are controlled by the catalyst. By the use of this protocol, a formal total synthesis of the polyketide cyanolide A was achieved with high diastereoselectivity and enantioselectivity.
Agid:
6363114