A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements

Mark S. Scott; Chris A. Luckhurst; Darren J. Dixon

doi:10.1021/ol052333c

A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements

Mark S. Scott, Chris A. Luckhurst, Darren J. Dixon

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

Abstract

(Chemical Equation Presented) A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and subsequent use of this stereocenter in a diastereoselective reductive cascade. This proceeded with unprecedentedly high stereocontrol and offered an elegant method of generating the desired syn stereochemistry present in the final target in one step. © 2005 American Chemical Society.

Original language	English
Pages (from-to)	5813-5816
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	26
DOIs	https://doi.org/10.1021/ol052333c
Publication status	Published - 22 Dec 2005

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title = "A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements",

abstract = "(Chemical Equation Presented) A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and subsequent use of this stereocenter in a diastereoselective reductive cascade. This proceeded with unprecedentedly high stereocontrol and offered an elegant method of generating the desired syn stereochemistry present in the final target in one step. {\textcopyright} 2005 American Chemical Society.",

author = "Scott, {Mark S.} and Luckhurst, {Chris A.} and Dixon, {Darren J.}",

year = "2005",

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T1 - A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements

AU - Scott, Mark S.

AU - Luckhurst, Chris A.

AU - Dixon, Darren J.

PY - 2005/12/22

Y1 - 2005/12/22

N2 - (Chemical Equation Presented) A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and subsequent use of this stereocenter in a diastereoselective reductive cascade. This proceeded with unprecedentedly high stereocontrol and offered an elegant method of generating the desired syn stereochemistry present in the final target in one step. © 2005 American Chemical Society.

AB - (Chemical Equation Presented) A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and subsequent use of this stereocenter in a diastereoselective reductive cascade. This proceeded with unprecedentedly high stereocontrol and offered an elegant method of generating the desired syn stereochemistry present in the final target in one step. © 2005 American Chemical Society.

U2 - 10.1021/ol052333c

DO - 10.1021/ol052333c

M3 - Article

SN - 1523-7052

VL - 7

SP - 5813

EP - 5816

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements

Abstract

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