From an ent -Estrane, through a nat -Androstane, to the Total Synthesis of the Marine-Derived Δ 8,9 -Pregnene (+)-03219A

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 pr...

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Bibliographic Details
Published in:Organic letters 2021-03, Vol.23 (6), p.2248-2252
Main Authors: Shalit, Zachary A, Valdes, Lucas C, Kim, Wan Shin, Micalizio, Glenn C
Format: Article
Language:English
Subjects:
Androstanes - chemical synthesis
Androstanes - chemistry
Estranes - chemistry
Molecular Structure
Pregnenes - chemical synthesis
Pregnenes - chemistry
Streptomyces - chemistry
Streptomyces - isolation & purification
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00382