An Iterative Phosphate Tether Mediated Approach for the Synthesis of Complex Polyol Subunits.

Org Lett

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.

Published: January 2022

A pot-economical approach to advanced polyol subunits is reported. The key reactions involved are iterative use of a phosphate tether-mediated one-pot sequential RCM/CM/H with subsequent utilization of either a regio-/diasteroselective cuprate addition or a Pd-catalyzed reductive allylic transposition. This method highlights the asymmetric synthesis of 12 complex polyol subunits in 4-6 one-pot sequential operations with a total of 12-14 reactions, of which 4-5 are catalytic, with minimal workup and purification procedures.

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http://dx.doi.org/10.1021/acs.orglett.1c03350DOI Listing

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