Acid catalysed rearrangements of the thevinols: The mechanism of furanocodide formation

Konstantinos Grivas; Simon W. Breeden; Christian Ganter; Stephen M. Husbands; John W. Lewis

doi:10.1016/S0040-4039(99)00012-X

Acid catalysed rearrangements of the thevinols: The mechanism of furanocodide formation

Konstantinos Grivas, Simon W. Breeden, Christian Ganter, Stephen M. Husbands, John W. Lewis

Research output: Contribution to journal › Article › peer-review

6 Citations (SciVal)

Abstract

The acid catalysed rearrangement of thevinols has been shown to proceed with retention of configuration at C-7 and therefore not via a sp2 hybridised centre at C-7 as had been proposed previously. Additionally a single diastereomer possessing the 20[R] configuration is formed in the rearrangements of the two diastereomeric i-propyl alcohols.

Original language	English
Pages (from-to)	1795-1798
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(99)00012-X
Publication status	Published - 26 Feb 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00012-X

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title = "Acid catalysed rearrangements of the thevinols: The mechanism of furanocodide formation",

abstract = "The acid catalysed rearrangement of thevinols has been shown to proceed with retention of configuration at C-7 and therefore not via a sp2 hybridised centre at C-7 as had been proposed previously. Additionally a single diastereomer possessing the 20[R] configuration is formed in the rearrangements of the two diastereomeric i-propyl alcohols.",

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AU - Grivas, Konstantinos

AU - Breeden, Simon W.

AU - Ganter, Christian

AU - Husbands, Stephen M.

AU - Lewis, John W.

PY - 1999/2/26

Y1 - 1999/2/26

N2 - The acid catalysed rearrangement of thevinols has been shown to proceed with retention of configuration at C-7 and therefore not via a sp2 hybridised centre at C-7 as had been proposed previously. Additionally a single diastereomer possessing the 20[R] configuration is formed in the rearrangements of the two diastereomeric i-propyl alcohols.

AB - The acid catalysed rearrangement of thevinols has been shown to proceed with retention of configuration at C-7 and therefore not via a sp2 hybridised centre at C-7 as had been proposed previously. Additionally a single diastereomer possessing the 20[R] configuration is formed in the rearrangements of the two diastereomeric i-propyl alcohols.

UR - https://www.scopus.com/pages/publications/0033605404

U2 - 10.1016/S0040-4039(99)00012-X

DO - 10.1016/S0040-4039(99)00012-X

M3 - Article

AN - SCOPUS:0033605404

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Acid catalysed rearrangements of the thevinols: The mechanism of furanocodide formation

Abstract

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