Concise synthesis of rodgersinol and determination of the C-10 absolute configuration

Seung Yong Seo; Jong Wha Jung; Jae Kyung Jung; Nam Jung Kim; Young Won Chin; Jinwoong Kim; Young Ger Suh

doi:10.1021/jo061980u

Concise synthesis of rodgersinol and determination of the C-10 absolute configuration

Seung Yong Seo, Jong Wha Jung, Jae Kyung Jung, Nam Jung Kim, Young Won Chin, Jinwoong Kim, Young Ger Suh

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Abstract

Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.

Original language	English
Pages (from-to)	666-668
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	72
Issue number	2
DOIs	https://doi.org/10.1021/jo061980u
State	Published - 19 Jan 2007

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abstract = "Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.",

author = "Seo, {Seung Yong} and Jung, {Jong Wha} and Jung, {Jae Kyung} and Kim, {Nam Jung} and Chin, {Young Won} and Jinwoong Kim and Suh, {Young Ger}",

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AU - Seo, Seung Yong

AU - Jung, Jong Wha

AU - Jung, Jae Kyung

AU - Kim, Nam Jung

AU - Chin, Young Won

AU - Kim, Jinwoong

AU - Suh, Young Ger

PY - 2007/1/19

Y1 - 2007/1/19

N2 - Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.

AB - Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.

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DO - 10.1021/jo061980u

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ER -

Concise synthesis of rodgersinol and determination of the C-10 absolute configuration

Abstract

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