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Org Lett. 2019 Apr 5;21(7):2369-2373. doi: 10.1021/acs.orglett.9b00650. Epub 2019 Mar 18.

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

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.

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