Stereoselectivity of model C22-23 aldol coupling for spirangiens A & B

Claire Gregg; Michael Perkins

doi:10.1016/j.tet.2012.10.008

Stereoselectivity of model C22-23 aldol coupling for spirangiens A & B

Claire Gregg, Michael Perkins

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

9 Citations (Scopus)

Abstract

A model system was prepared to investigate the diastereoselectivity of the key C22-23 aldol coupling for the synthesis of spirangiens A & B. The lithium enolate of model ketone 3 was coupled with the differently protected aldehydes 4 (acetonide) and 5 (silyl) giving 3:1 and 3.5:1 dr, respectively, in favour of the unnatural (S) isomer in both cases. The lack of any significant effect on the aldol stereoselectivity induced by the aldehyde protecting groups contrasts with previous literature reports.

Original language	English
Pages (from-to)	387-394
Number of pages	8
Journal	Tetrahedron
Volume	69
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2012.10.008
Publication status	Published - 7 Jan 2013

Keywords

Aldol reaction
Cytotoxic
Polyketide
Spirangien
Spiroacetal

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10.1016/j.tet.2012.10.008

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abstract = "A model system was prepared to investigate the diastereoselectivity of the key C22-23 aldol coupling for the synthesis of spirangiens A & B. The lithium enolate of model ketone 3 was coupled with the differently protected aldehydes 4 (acetonide) and 5 (silyl) giving 3:1 and 3.5:1 dr, respectively, in favour of the unnatural (S) isomer in both cases. The lack of any significant effect on the aldol stereoselectivity induced by the aldehyde protecting groups contrasts with previous literature reports.",

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AB - A model system was prepared to investigate the diastereoselectivity of the key C22-23 aldol coupling for the synthesis of spirangiens A & B. The lithium enolate of model ketone 3 was coupled with the differently protected aldehydes 4 (acetonide) and 5 (silyl) giving 3:1 and 3.5:1 dr, respectively, in favour of the unnatural (S) isomer in both cases. The lack of any significant effect on the aldol stereoselectivity induced by the aldehyde protecting groups contrasts with previous literature reports.

KW - Aldol reaction

KW - Cytotoxic

KW - Polyketide

KW - Spirangien

KW - Spiroacetal

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JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Stereoselectivity of model C22-23 aldol coupling for spirangiens A & B

Abstract

Keywords

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