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

40 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

Access to Document

10.1021/ol701564x

Cite this

@article{7fece365179f4ce5b36109f8a06bb6c6,

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

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",

month = aug,

day = "16",

doi = "10.1021/ol701564x",

language = "English (US)",

volume = "9",

pages = "3481--3483",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

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

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/34548165787

UR - https://www.scopus.com/inward/citedby.url?scp=34548165787&partnerID=8YFLogxK

U2 - 10.1021/ol701564x

DO - 10.1021/ol701564x

M3 - Article

C2 - 17658844

AN - SCOPUS:34548165787

SN - 1523-7060

VL - 9

SP - 3481

EP - 3483

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this