Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin

Deb K. Barma; Biao Lu; Rachid Baati; Charles Mioskowski; J R Falck

doi:10.1016/j.tetlet.2008.05.026

Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin

Deb K. Barma, Biao Lu, Rachid Baati, Charles Mioskowski, J R Falck

Biochemistry

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

7 Scopus citations

Abstract

The CrCl₂-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.

Original language	English (US)
Pages (from-to)	4359-4361
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	28
DOIs	https://doi.org/10.1016/j.tetlet.2008.05.026
State	Published - Jul 7 2008

Keywords

Aldehydes
Chromium
Enals
Homologation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.05.026

Cite this

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title = "Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin",

abstract = "The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.",

keywords = "Aldehydes, Chromium, Enals, Homologation",

author = "Barma, {Deb K.} and Biao Lu and Rachid Baati and Charles Mioskowski and Falck, {J R}",

note = "Funding Information: Financial support provided by the CNRS, the Robert A. Welch Foundation, and NIH (DK38226, GM31278) is gratefully acknowledged. ",

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T1 - Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes

T2 - synthesis of a Laurencia flexilis toxin

AU - Barma, Deb K.

AU - Lu, Biao

AU - Baati, Rachid

AU - Mioskowski, Charles

AU - Falck, J R

N1 - Funding Information: Financial support provided by the CNRS, the Robert A. Welch Foundation, and NIH (DK38226, GM31278) is gratefully acknowledged.

PY - 2008/7/7

Y1 - 2008/7/7

N2 - The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.

AB - The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.

KW - Aldehydes

KW - Chromium

KW - Enals

KW - Homologation

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DO - 10.1016/j.tetlet.2008.05.026

M3 - Article

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SN - 0040-4039

VL - 49

SP - 4359

EP - 4361

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin

Abstract

Keywords

ASJC Scopus subject areas

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