Intramolecular allenolate acylations in studies toward a synthesis of FR182877

Christopher D. Vanderwal; David A. Vosburg; Erik J. Sorensen

doi:10.1021/ol016994v

Intramolecular allenolate acylations in studies toward a synthesis of FR182877

Christopher D. Vanderwal, David A. Vosburg, Erik J. Sorensen

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47 Scopus citations

Abstract

(Matrix Presented) During our efforts to synthesize the cytotoxic natural product FR182877, we discovered intramolecular reductive acylations that offer a stereocontrolled alternative to the classical Knoevenagel condensation for the formation of α-alkylidene β-keto-δ-lactones. Other progress toward a synthesis of FR182877 includes a π-allyl Stille coupling and a bromo Horner-Wadsworth-Emmons reaction that forms a 12-membered ring. Structural relationships among FR182877, hexacyclinic acid, macquarimicin A, and cochleamycin A are also discussed.

Original language	English (US)
Pages (from-to)	4307-4310
Number of pages	4
Journal	Organic letters
Volume	3
Issue number	26
DOIs	https://doi.org/10.1021/ol016994v
State	Published - Dec 27 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016994v

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title = "Intramolecular allenolate acylations in studies toward a synthesis of FR182877",

abstract = "(Matrix Presented) During our efforts to synthesize the cytotoxic natural product FR182877, we discovered intramolecular reductive acylations that offer a stereocontrolled alternative to the classical Knoevenagel condensation for the formation of α-alkylidene β-keto-δ-lactones. Other progress toward a synthesis of FR182877 includes a π-allyl Stille coupling and a bromo Horner-Wadsworth-Emmons reaction that forms a 12-membered ring. Structural relationships among FR182877, hexacyclinic acid, macquarimicin A, and cochleamycin A are also discussed.",

author = "Vanderwal, {Christopher D.} and Vosburg, {David A.} and Sorensen, {Erik J.}",

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language = "English (US)",

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AU - Vosburg, David A.

AU - Sorensen, Erik J.

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Y1 - 2001/12/27

N2 - (Matrix Presented) During our efforts to synthesize the cytotoxic natural product FR182877, we discovered intramolecular reductive acylations that offer a stereocontrolled alternative to the classical Knoevenagel condensation for the formation of α-alkylidene β-keto-δ-lactones. Other progress toward a synthesis of FR182877 includes a π-allyl Stille coupling and a bromo Horner-Wadsworth-Emmons reaction that forms a 12-membered ring. Structural relationships among FR182877, hexacyclinic acid, macquarimicin A, and cochleamycin A are also discussed.

AB - (Matrix Presented) During our efforts to synthesize the cytotoxic natural product FR182877, we discovered intramolecular reductive acylations that offer a stereocontrolled alternative to the classical Knoevenagel condensation for the formation of α-alkylidene β-keto-δ-lactones. Other progress toward a synthesis of FR182877 includes a π-allyl Stille coupling and a bromo Horner-Wadsworth-Emmons reaction that forms a 12-membered ring. Structural relationships among FR182877, hexacyclinic acid, macquarimicin A, and cochleamycin A are also discussed.

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Intramolecular allenolate acylations in studies toward a synthesis of FR182877

Abstract

All Science Journal Classification (ASJC) codes

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