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  Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin

Schaubach, S., Michigami, K., & Fürstner, A. (2017). Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin. Synthesis, 48(1), 202-208. doi:10.1055/s-0035-1562381.

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 Creators:
Schaubach, Sebastian1, Author              
Michigami, Kenichi1, 2, Author              
Fürstner, Alois1, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, ou_persistent22              

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Free keywords: alkyne metathesis - enynes - hydrostannation - molybdenum alkylidynes - natural products - ruthenium - trans-reduction
 Abstract: 1,3-Enynes are hardly amenable to trans-hydrometalation reactions, because they tend to bind the standard ruthenium catalysts too tightly. However, catalysts comprising a [Cp*Ru–Cl] unit allow such compounds to be used, provided they contain an OH group next to the triple bond. This aspect is illustrated by a formal synthesis of the lichen-derived macrolide aspicilin. The required macrocyclic enyne precursor was formed by an efficient ring-closing alkyne metathesis reaction.

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Language(s): eng - English
 Dates: 2016-06-212016-06-212016-07-042017-01-03
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-0035-1562381
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Title: Synthesis
Source Genre: Journal
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Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: 48 (1) Sequence Number: - Start / End Page: 202 - 208 Identifier: ISSN: 0039-7881
CoNE: https://pure.mpg.de/cone/journals/resource/954925448757