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Org Lett ; 21(7): 2369-2373, 2019 04 05.
Article in English | MEDLINE | ID: mdl-30883133

ABSTRACT

An iterative protocol was developed for highly diastereo- and enantioselective construction of high-order 1,3-polyols via iridium-catalyzed asymmetric hydrogenation of ß-alkyl-ß-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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