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  Concise Total Synthesis of Ivorenolide B

Ungeheuer, F., & Fürstner, A. (2015). Concise Total Synthesis of Ivorenolide B. Chemistry – A European Journal, 21(32), 11387-11392. doi:10.1002/chem.201501765.

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Ungeheuer, Felix1, 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; molybdenum; natural products; total synthesis
 Abstract: An expeditious route to the potential immunosuppressive lead compound ivorenolide B (1) is described, which relies on the formation of the distinctive 1,3-diyne subunit embedded into the 17-membered framework of this target by ring-closing alkyne metathesis (RCAM). This key transformation was accomplished with the aid of the molybdenum alkylidyne complex 7, which turned out to be compatible with the acid sensitive propargylic alcohol substituents as well as the terminal alkyne unit present in the cyclization precursor. As the presence of such functionality had been detrimental for alkyne metathesis until very recently, this example illustrates the excellent application profile of this new catalyst as well as the rapidly increasing scope of the transformation. Its structural outreach can be further increased by subjecting cyclo-1,3-diynes to appropriate post-metathetic transformations, most notably with the help of alkynophilic gold or palladium catalysts. This aspect is illustrated by the conversion of the model compound 4 into various cyclophane products.

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Language(s): eng - English
 Dates: 2015-05-062015-07-032015-08-03
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201501765
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 21 (32) Sequence Number: - Start / End Page: 11387 - 11392 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058