Synthetic studies toward swinhoeisterol A, a novel steroid with an unusual carbon skeleton

[Display omitted] •Swinhoeisterol A is a novel marine sterol with an unusual 6/6/5/7 tetracyclic skeleton.•We have developed access to a tricyclic compound with BCD rings of swinhoeisterol A.•Friedel–Crafts acylation and an oxidative dearomatization are the key steps.•The strategy was applied to a s...

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Bibliographic Details
Published in:Tetrahedron letters 2019-02, Vol.60 (8), p.591-593
Main Authors: Takano, Atsuhiro, Zhao, Yiwen, Ohyoshi, Takayuki, Kigoshi, Hideo
Format: Article
Language:English
Subjects:
6/65/7
Steroid
Swinhoeisterol A
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Summary:[Display omitted] •Swinhoeisterol A is a novel marine sterol with an unusual 6/6/5/7 tetracyclic skeleton.•We have developed access to a tricyclic compound with BCD rings of swinhoeisterol A.•Friedel–Crafts acylation and an oxidative dearomatization are the key steps.•The strategy was applied to a similar 6/5/6-tricyclic system. Swinhoeisterol A is a novel steroid with unusual 6/6/5/7 tetracyclic skeleton. The model compound with BCD rings is constructed by Friedel–Crafts acylation and an oxidative dearomatization as key steps.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.01.027