Towards the total synthesis of calyculin C: Preparation of the C9-C25 spiroketal-dipropionate unit

Habrant, Damien; Koskinen, Ari M.P.

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Towards the total synthesis of calyculin C: Preparation of the C9-C25 spiroketal-dipropionate unit

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Title:	Towards the total synthesis of calyculin C: Preparation of the C9-C25 spiroketal-dipropionate unit
Author(s):	Habrant, Damien ; Koskinen, Ari M.P.
Date:	2010
Language:	en
Pages:	4364-4373
Department:	School services, CHEM Department of Chemistry Department of Chemistry and Materials Science Organic Chemistry
Series:	ORGANIC AND BIOMOLECULAR CHEMISTRY, Volume 8, issue 19
ISSN:	1477-0520 1477-0539
DOI-number:	10.1039/c0ob00092b
Subject:	116 Chemical sciences
Keywords:	116 Chemical sciences
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Citation: Habrant , D & Koskinen , A M P 2010 , ' Towards the total synthesis of calyculin C: Preparation of the C9-C25 spiroketal-dipropionate unit ' ORGANIC AND BIOMOLECULAR CHEMISTRY , vol 8 , no. 19 , pp. 4364-4373 . DOI: 10.1039/c0ob00092b
Abstract: An asymmetric synthesis of the C9 –C25 spiroketal fragment of calyculin C is described. Key steps include two crotylation reactions using successively Brown’s reagent and (Z)-crotyltrifluorosilane for the formation of the anti, anti, anti stereotetrad, ynone formation by a Pd-catalyzed coupling of a thiol ester with a terminal alkyne and a double intramolecular hetero-Michael addition for the stereoselective construction of the spiroketal framework.

Permanent link to this item: http://urn.fi/URN:NBN:fi:aalto-201609163824 Email this Export to RefWorks QR Code Print BibTex Tweet