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

AI Article Synopsis

  • The study details the total synthesis of (+)-03219A, a rare Δ-pregnene from the marine species SCSIO 03219.
  • The synthesis involves multiple transformation steps, starting from epichlorohydrin and progressing through several steroid frameworks, culminating in the natural product.
  • Two critical rearrangement processes were essential for inverting the quaternary center at C13 and establishing the quaternary center at C10.

Article Abstract

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

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