Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction

Yen Jin Chin; Shun Yi Wang; Teck Peng Loh

doi:10.1021/ol901480s

Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction

Yen Jin Chin^*, Shun Yi Wang, Teck Peng Loh

^*Corresponding author for this work

Nanyang Technological University

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

35 Citations (Scopus)

Abstract

Image Presented The key C13-C23 fragment toward the total synthesis of iriomoteolide-1a (1) has been constructed from an 1,2-acetonide containing aldehyde 5 via a Julia-Kocienski olefination with the C16-C23 segment 6. The key step involves stereoselective introduction of the C29 methyl group by a highly efficient CuI-Tol-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to an α,β-unsaturated ester.

Original language	English
Pages (from-to)	3674-3676
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	16
DOIs	https://doi.org/10.1021/ol901480s
Publication status	Published - Aug 20 2009
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol901480s

Cite this

@article{dbd25f218d9f4207aa2cad0b44675eaa,

title = "Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction",

abstract = "Image Presented The key C13-C23 fragment toward the total synthesis of iriomoteolide-1a (1) has been constructed from an 1,2-acetonide containing aldehyde 5 via a Julia-Kocienski olefination with the C16-C23 segment 6. The key step involves stereoselective introduction of the C29 methyl group by a highly efficient CuI-Tol-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to an α,β-unsaturated ester.",

author = "Chin, {Yen Jin} and Wang, {Shun Yi} and Loh, {Teck Peng}",

year = "2009",

month = aug,

day = "20",

doi = "10.1021/ol901480s",

language = "English",

volume = "11",

pages = "3674--3676",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction

AU - Chin, Yen Jin

AU - Wang, Shun Yi

AU - Loh, Teck Peng

PY - 2009/8/20

Y1 - 2009/8/20

N2 - Image Presented The key C13-C23 fragment toward the total synthesis of iriomoteolide-1a (1) has been constructed from an 1,2-acetonide containing aldehyde 5 via a Julia-Kocienski olefination with the C16-C23 segment 6. The key step involves stereoselective introduction of the C29 methyl group by a highly efficient CuI-Tol-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to an α,β-unsaturated ester.

AB - Image Presented The key C13-C23 fragment toward the total synthesis of iriomoteolide-1a (1) has been constructed from an 1,2-acetonide containing aldehyde 5 via a Julia-Kocienski olefination with the C16-C23 segment 6. The key step involves stereoselective introduction of the C29 methyl group by a highly efficient CuI-Tol-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to an α,β-unsaturated ester.

UR - http://www.scopus.com/inward/record.url?scp=68949109676&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=68949109676&partnerID=8YFLogxK

U2 - 10.1021/ol901480s

DO - 10.1021/ol901480s

M3 - Article

C2 - 19627100

AN - SCOPUS:68949109676

SN - 1523-7060

VL - 11

SP - 3674

EP - 3676

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this