Total synthesis of Brevetoxin A

Michael T. Crimmins; J. Lucas Zuccarello; J. Michael Ellis; Patrick J. McDougall; Pamela A. Haile; Jonathan D. Parrish; Kyle A. Emmitte

doi:10.1021/ol802710u

Total synthesis of Brevetoxin A

Michael T. Crimmins, J. Lucas Zuccarello, J. Michael Ellis, Patrick J. McDougall, Pamela A. Haile, Jonathan D. Parrish, Kyle A. Emmitte

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Abstract

(Chemical Equation Presented) A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

Original language	English
Pages (from-to)	489-492
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	2
DOIs	https://doi.org/10.1021/ol802710u
State	Published - 15 Jan 2009

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abstract = "(Chemical Equation Presented) A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.",

author = "Crimmins, {Michael T.} and Zuccarello, {J. Lucas} and Ellis, {J. Michael} and McDougall, {Patrick J.} and Haile, {Pamela A.} and Parrish, {Jonathan D.} and Emmitte, {Kyle A.}",

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AU - Crimmins, Michael T.

AU - Zuccarello, J. Lucas

AU - Ellis, J. Michael

AU - McDougall, Patrick J.

AU - Haile, Pamela A.

AU - Parrish, Jonathan D.

AU - Emmitte, Kyle A.

PY - 2009/1/15

Y1 - 2009/1/15

N2 - (Chemical Equation Presented) A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

AB - (Chemical Equation Presented) A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

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JO - Organic Letters

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ER -

Total synthesis of Brevetoxin A

Abstract

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