An efficient and enantioselective total synthesis of naturally occurring L-783277

Hwan Geun Choi; Jung Beom Son; Dong Sik Park; Young Jin Ham; Jung Mi Hah; Taebo Sim

doi:10.1016/j.tetlet.2010.07.122

An efficient and enantioselective total synthesis of naturally occurring L-783277

Hwan Geun Choi, Jung Beom Son, Dong Sik Park, Young Jin Ham, Jung Mi Hah, Taebo Sim

KU-KIST Graduate School of Converging Science and Technology

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

16 Citations (Scopus)

Abstract

Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.

Original language	English
Pages (from-to)	4942-4946
Number of pages	5
Journal	Tetrahedron Letters
Volume	51
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.122
Publication status	Published - 2010

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MODHRD, KRF-2007-355-C00027).

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.07.122

Cite this

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title = "An efficient and enantioselective total synthesis of naturally occurring L-783277",

abstract = "Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.",

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T1 - An efficient and enantioselective total synthesis of naturally occurring L-783277

AU - Choi, Hwan Geun

AU - Son, Jung Beom

AU - Park, Dong Sik

AU - Ham, Young Jin

AU - Hah, Jung Mi

AU - Sim, Taebo

N1 - Funding Information: This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MODHRD, KRF-2007-355-C00027).

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Y1 - 2010

N2 - Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.

AB - Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.

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DO - 10.1016/j.tetlet.2010.07.122

M3 - Article

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SN - 0040-4039

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JO - Tetrahedron Letters

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An efficient and enantioselective total synthesis of naturally occurring L-783277

Abstract

Bibliographical note

ASJC Scopus subject areas

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