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  Formal total synthesis of ascidiatrienolide A and the didemnilactones

Fürstner, A., & Schlede, M. (2002). Formal total synthesis of ascidiatrienolide A and the didemnilactones. Advanced Synthesis & Catalysis, 344(6-7), 657-665. doi:10.1002/1615-4169(200208)344:6/7<657:AID-ADSC657>3.0.CO;2-0.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-000F-99B2-B Version Permalink: http://hdl.handle.net/11858/00-001M-0000-001A-2A55-2
Genre: Journal Article

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 Creators:
Fürstner, A.1, Author              
Schlede, M.1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: medium-sized rings; metathesis; natural products; ruthenium; stereochemistry
 Abstract: A concise synthesis of the ten-membered lactone 26 is described which constitutes the key intermediate of a previous total synthesis of the marine natural product ascidiatrienolide 1 and can also be elaborated into the closely related didemnilactones 2 - 4. The E/Z-ratio obtained in the ring-closing metathesis (RCM) reaction forging such non-enolide structures is found to be dependent on the relative configuration of the cyclization precursor as well as on the chosen catalyst. Specifically, it is shown that the ruthenium indenylidene complex 12 and the "second generation" Grubbs type catalyst 13 bearing an N- heterocyclic carbene ligand lead to opposite stereochemical results when applied to the synconfigured diene 21, but to the identical outcome with the anti-configured analogue 10.

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Language(s): eng - English
 Dates: 2002-08
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Degree: -

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Title: Advanced Synthesis & Catalysis
  Alternative Title : Adv. Synth. Catal.
Source Genre: Journal
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Publ. Info: -
Pages: - Volume / Issue: 344 (6-7) Sequence Number: - Start / End Page: 657 - 665 Identifier: ISSN: 1615-4150