Organic Chemistry

Eleven-Step Chemoenzymatic Synthesis of Cotylenol

Authors

Abstract

Cotylenin A and fusicoccin A are two flagship members of the fusicoccane diterpenoid family that are capable of acting as molecular glues to stabilize the interaction between the 14-3-3 proteins and their clients. Herein, we report a concise che-moenzymatic synthesis of cotylenol, the aglycone of cotylenin A. Key features that contribute to the brevity of the route include the union of two cyclopentene fragments in an allylative coupling, a one-pot Prins cyclization-transannular hydride shift sequence, and a late-stage enzymatic oxidation to install the key tertiary alcohol at C3.

Content

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Supplementary material

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Supporting Information for Eleven-Step Chemoenzymatic Synthesis of Cotylenol
DNA sequences and experimental procedures