From an -Estrane, through a -Androstane, to the Total Synthesis of the Marine-Derived Δ-Pregnene (+)-03219A.

Org Lett

Department of Chemistry, Dartmouth College, Burke Laboratory, Hanover, New Hampshire 03755, United States.

Published: March 2021

The total synthesis of (+)-03219A, a rare Δ-pregnene isolated from the marine-derived sp. SCSIO 03219, is described that is based on a series of transformations that enable progression from epichlorohydrin to an -estrane, then conversion to a -androstane, and finally establishment of the natural product target. Key to the success of these studies was implementation of two rearrangement processes to formally invert the quaternary center at C13 and establish the C10 quaternary center.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8420867PMC
http://dx.doi.org/10.1021/acs.orglett.1c00382DOI Listing

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