A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

Choong Eui Song; Sung Woo Lee; Eun Joo Roh; Sang Gi Lee; Won Ku Lee

doi:10.1016/S0957-4166(98)00049-4

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

Choong Eui Song
, Sung Woo Lee
, Eun Joo Roh
, Sang Gi Lee
, Won Ku Lee

Department of Chemistry & Nanoscience

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

31 Scopus citations

Abstract

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one, an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo- 3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation.

Original language	English
Pages (from-to)	983-992
Number of pages	10
Journal	Tetrahedron Asymmetry
Volume	9
Issue number	6
DOIs	https://doi.org/10.1016/S0957-4166(98)00049-4
State	Published - 27 Mar 1998

Bibliographical note

Funding Information:
This work was supported by a grant from Ministry of Science and Technology in Korea. The authors also thank Dr. Chong-Gi Hong for HRMS analyses of 10b , c .

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title = "A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor",

abstract = "A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one, an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo- 3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation.",

author = "Song, \{Choong Eui\} and Lee, \{Sung Woo\} and Roh, \{Eun Joo\} and Lee, \{Sang Gi\} and Lee, \{Won Ku\}",

note = "Funding Information: This work was supported by a grant from Ministry of Science and Technology in Korea. The authors also thank Dr. Chong-Gi Hong for HRMS analyses of 10b , c . ",

year = "1998",

month = mar,

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doi = "10.1016/S0957-4166(98)00049-4",

language = "English",

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T1 - A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

AU - Song, Choong Eui

AU - Lee, Sung Woo

AU - Roh, Eun Joo

AU - Lee, Sang Gi

AU - Lee, Won Ku

N1 - Funding Information: This work was supported by a grant from Ministry of Science and Technology in Korea. The authors also thank Dr. Chong-Gi Hong for HRMS analyses of 10b , c .

PY - 1998/3/27

Y1 - 1998/3/27

N2 - A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one, an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo- 3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation.

AB - A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one, an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo- 3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation.

UR - https://www.scopus.com/pages/publications/0344269324

U2 - 10.1016/S0957-4166(98)00049-4

DO - 10.1016/S0957-4166(98)00049-4

M3 - Article

AN - SCOPUS:0344269324

SN - 0957-4166

VL - 9

SP - 983

EP - 992

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 6

ER -

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

Abstract

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