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  Total Syntheses of Scabrolide A and Nominal Scabrolide B

Meng, Z., & Fürstner, A. (2022). Total Syntheses of Scabrolide A and Nominal Scabrolide B. Journal of the American Chemical Society, 144(4), 1528-1533. doi:10.1021/jacs.1c12401.

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ja1c12401_si_001-1.pdf (Supplementary material), 15MB
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 Creators:
Meng, Zhanchao1, Author              
Fürstner, Alois1, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: 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.

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Language(s): eng - English
 Dates: 2021-11-242022-01-192022-02-02
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.1c12401
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 144 (4) Sequence Number: - Start / End Page: 1528 - 1533 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870