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  trans-Hydrogenation: Application to a Concise and Scalable Synthesis of Brefeldin A

Fuchs, M., & Fürstner, A. (2015). trans-Hydrogenation: Application to a Concise and Scalable Synthesis of Brefeldin A. Angewandte Chemie International Edition, 54(13), 3978-3982. doi:10.1002/anie.201411618.

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 Creators:
Fuchs, Michael1, 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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Free keywords: alkyne metathesis; hydrogenation; natural products; ruthenium; total synthesis
 Abstract: The important biochemical probe molecule brefeldin A (1) has served as an inspirational target in the past, but none of the many routes has actually delivered more than just a few milligrams of product, where documented. The approach described herein is clearly more efficient; it hinges upon the first implementation of ruthenium-catalyzed trans-hydrogenation in natural products total synthesis. Because this unorthodox reaction is selective for the triple bond and does not touch the transannular alkene or the lactone site of the cycloalkyne, it outperforms the classical Birch-type reduction that could not be applied at such a late stage. Other key steps en route to 1 comprise an iron-catalyzed reductive formation of a non-terminal alkyne, an asymmetric propiolate carbonyl addition mediated by a bulky amino alcohol, and a macrocyclization by ring-closing alkyne metathesis catalyzed by a molybdenum alkylidyne.

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Language(s): eng - English
 Dates: 2014-12-022015-02-042015-03-23
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201411618
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH Verlag GmbH & Co. KGaA
Pages: - Volume / Issue: 54 (13) Sequence Number: - Start / End Page: 3978 - 3982 Identifier: ISSN: 1521-3773
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833