Total synthesis of solandelactones E and F, homoeicosanoids from the hydroid Solanderia secunda

James D. White; William H.C. Martin; Christopher Lincoln; Jongtae Yang

doi:10.1021/ol701564x

Total synthesis of solandelactones E and F, homoeicosanoids from the hydroid Solanderia secunda

James D. White, William H.C. Martin, Christopher Lincoln, Jongtae Yang

Houston Methodist

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

36 Scopus citations

Abstract

Asymmetrie total syntheses of solandelactones E and F confirmed that hydroxyl configuration at C11 in these oxylipins had been misassigned and that the stereochemistry at this center should be reversed. Key steps in the synthesis involved a Nagao asymmetric acetate aldol reaction, a directed Simmons-Smith cyclopropanation, a Holmes-Claisen rearrangement to establish the unsaturated octalactone, and a Nozaki-Hiyama-Kishi coupling to connect two major fragments at C11-C12.

Original language	English (US)
Pages (from-to)	3481-3483
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	17
DOIs	https://doi.org/10.1021/ol701564x
State	Published - Aug 16 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Asymmetrie total syntheses of solandelactones E and F confirmed that hydroxyl configuration at C11 in these oxylipins had been misassigned and that the stereochemistry at this center should be reversed. Key steps in the synthesis involved a Nagao asymmetric acetate aldol reaction, a directed Simmons-Smith cyclopropanation, a Holmes-Claisen rearrangement to establish the unsaturated octalactone, and a Nozaki-Hiyama-Kishi coupling to connect two major fragments at C11-C12.",

author = "White, {James D.} and Martin, {William H.C.} and Christopher Lincoln and Jongtae Yang",

year = "2007",

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T1 - Total synthesis of solandelactones E and F, homoeicosanoids from the hydroid Solanderia secunda

AU - White, James D.

AU - Martin, William H.C.

AU - Lincoln, Christopher

AU - Yang, Jongtae

PY - 2007/8/16

Y1 - 2007/8/16

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AB - Asymmetrie total syntheses of solandelactones E and F confirmed that hydroxyl configuration at C11 in these oxylipins had been misassigned and that the stereochemistry at this center should be reversed. Key steps in the synthesis involved a Nagao asymmetric acetate aldol reaction, a directed Simmons-Smith cyclopropanation, a Holmes-Claisen rearrangement to establish the unsaturated octalactone, and a Nozaki-Hiyama-Kishi coupling to connect two major fragments at C11-C12.

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JF - Organic Letters

SN - 1523-7060

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Total synthesis of solandelactones E and F, homoeicosanoids from the hydroid Solanderia secunda

Abstract

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