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

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

16 Scopus citations

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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title = "Concise synthesis of rodgersinol and determination of the C-10 absolute configuration",

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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T1 - Concise synthesis of rodgersinol and determination of the C-10 absolute configuration

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.

UR - https://www.scopus.com/pages/publications/33846206107

U2 - 10.1021/jo061980u

DO - 10.1021/jo061980u

M3 - Article

C2 - 17221994

AN - SCOPUS:33846206107

SN - 0022-3263

VL - 72

SP - 666

EP - 668

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

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

Abstract

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