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  Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide

Fürstner, A., & Dierkes, T. (2000). Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide. Organic Letters, 2(16), 2463-2465. doi:10.1021/ol006122d.

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[120]SI.pdf (Supplementary material), 57KB
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 Creators:
Fürstner, Alois1, Author              
Dierkes, Thorsten1, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: A concise total synthesis of the bis-butenolide 3 in optically active form is reported. Key steps are a zinc-mediated “three-component coupling” with formation of dienyne 9 which undergoes ring closing metathesis (RCM) on treatment with (PCy3)2Cl2Ru=CHPh. Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)3WΞCCMe3 as the catalyst. A Lindlar reduction completes this synthesis which delivers product 3 in only five steps with an overall yield of 25%.

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Language(s): eng - English
 Dates: 2000-05-292000-07-132000-08-10
 Publication Status: Published in print
 Pages: 3
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ol006122d
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: 3 Volume / Issue: 2 (16) Sequence Number: - Start / End Page: 2463 - 2465 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338