A stereoselective cyclisation cascade mediated by SmI2-H 2O: Synthetic studies towards stolonidiol

Thomas M. Baker; Lisa A. Sloan; Lokman H. Choudhury; Masahito Murai; David J. Procter

doi:10.1016/j.tetasy.2010.03.047

A stereoselective cyclisation cascade mediated by SmI2-H 2O: Synthetic studies towards stolonidiol

Thomas M. Baker, Lisa A. Sloan, Lokman H. Choudhury, Masahito Murai, David J. Procter

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Abstract

A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. © 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1246-1261
Number of pages	15
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	9-10
DOIs	https://doi.org/10.1016/j.tetasy.2010.03.047
Publication status	Published - 17 May 2010

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CCDC 747958: Experimental Crystal Structure Determination
Baker, T. M. (Contributor), Sloan, L. A. (Contributor), Choudhury, L. H. (Contributor), Murai, M. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2011
DOI: 10.5517/cct39pw, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cct39pw&sid=DataCite
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abstract = "A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. {\textcopyright} 2010 Elsevier Ltd. All rights reserved.",

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AU - Baker, Thomas M.

AU - Sloan, Lisa A.

AU - Choudhury, Lokman H.

AU - Murai, Masahito

AU - Procter, David J.

PY - 2010/5/17

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N2 - A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. © 2010 Elsevier Ltd. All rights reserved.

AB - A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. © 2010 Elsevier Ltd. All rights reserved.

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DO - 10.1016/j.tetasy.2010.03.047

M3 - Article

SN - 0957-4166

VL - 21

SP - 1246

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 9-10

ER -

A stereoselective cyclisation cascade mediated by SmI2-H 2O: Synthetic studies towards stolonidiol

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CCDC 747958: Experimental Crystal Structure Determination

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