Total Syntheses of Scabrolide A and Nominal Scabrolide B

The marine natural product scabrolide A was obtained by isomerization of the vinylogous 1,4-diketone entity of nominal scabrolide B as the purported pivot point of the biosynthesis of these polycyclic norcembranoids. Despite the success of this maneuver, the latter compound itself turned out not to...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 144; no. 4; pp. 1528 - 1533
Main Authors Meng, Zhanchao, Fuerstner, Alois
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 02.02.2022
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
NORDITERPENOIDS
YONAROLIDE
SOFT CORAL
REARRANGEMENTS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
METATHESIS
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Summary:The marine natural product scabrolide A was obtained by isomerization of the vinylogous 1,4-diketone entity of nominal scabrolide B as the purported pivot point of the biosynthesis of these polycyclic norcembranoids. Despite the success of this maneuver, the latter compound itself turned out not to be identical with the natural product of that name. The key steps en route to the carbocyclic core of these targets were a [2,3]-sigmatropic rearrangement of an allylic sulfur ylide to forge the overcrowded C12-C13 bond, an RCM reaction to close the congested central six-membered ring, and a hydroxy-directed epoxidation/epoxide opening/isomerization sequence to set the "umpoled" 1,4-dicarbonyl motif and the correct angular configuration at C12.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c12401