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  Diastereoselctive Synthesis of Enantiopure γ–Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures

Macabeo, A. P. G., Lehmann, C. W., & Reiser, O. (2012). Diastereoselctive Synthesis of Enantiopure γ–Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures. Synlett, 23(20), 2909-2912. doi:10.1055/s-0032-1317555.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000E-EBBE-E Version Permalink: https://hdl.handle.net/21.11116/0000-0007-1E4D-3
Genre: Journal Article

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 Creators:
Macabeo, Allan Patrick G.1, 2, Author
Lehmann, Christian W.3, Author           
Reiser, Oliver1, Author
Affiliations:
1Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany, ou_persistent22              
2Organic Synthesis Laboratory, Research Center for the Natural and Applied Sciences, University of Santo Tomas, Espana St., Manila 1015, Philippines, ou_persistent22              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: marine furanocembranoids; asymmetric synthesis; ­vinylogous Mukaiyama addition; lactones; furans
 Abstract: A diastereoselective methodology for preparing trans-γ-lactone-γ-butenolides through vinylogous aldol additions of siloxyfuranes to enantiopure cyclopropylcarbaldehyde followed by a tin-catalyzed retroaldol-lactonization cascade is reported. This synthetic approach is applied to a short synthesis of an exo-trienol furan lactone substructure relevant to bielschowskysin and other related coral diterpenoid natural products.

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Language(s): eng - English
 Dates: 2012-12-16
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-0032-1317555
 Degree: -

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Title: Synlett
  Other : Synlett
Source Genre: Journal
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Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: 23 (20) Sequence Number: - Start / End Page: 2909 - 2912 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856