Synthesis of novel thiol taxoids based on the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III: Both the syn and anti 10-deacetyl-2′-deoxy-2′-mercaptopaclitaxels

Xin Qi; Sang Hyeup Lee; Juyoung Yoon; Yoon Sik Lee

doi:10.1016/j.tet.2004.03.064

Synthesis of novel thiol taxoids based on the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III: Both the syn and anti 10-deacetyl-2′-deoxy-2′-mercaptopaclitaxels

Xin Qi, Sang Hyeup Lee, Juyoung Yoon, Yoon Sik Lee

Department of Chemistry & Nanoscience

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

2 Scopus citations

Abstract

Two new kinds of docetaxel compound, with a mercapto group instead of the hydroxyl on the C13 side chain (both syn and anti), via the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III route, were synthesized. The uses of trans and cis oxazoline compounds, and their stereoselective ring-opening reactions with thiolacetic acid, were proved to be key steps.

Original language	English
Pages (from-to)	4133-4138
Number of pages	6
Journal	Tetrahedron
Volume	60
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2004.03.064
State	Published - 3 May 2004

Bibliographical note

Funding Information:
We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.

Keywords

Mercapto taxoid
Oxazoline
Taxol

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10.1016/j.tet.2004.03.064

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title = "Synthesis of novel thiol taxoids based on the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III: Both the syn and anti 10-deacetyl-2′-deoxy-2′-mercaptopaclitaxels",

abstract = "Two new kinds of docetaxel compound, with a mercapto group instead of the hydroxyl on the C13 side chain (both syn and anti), via the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III route, were synthesized. The uses of trans and cis oxazoline compounds, and their stereoselective ring-opening reactions with thiolacetic acid, were proved to be key steps.",

keywords = "Mercapto taxoid, Oxazoline, Taxol",

author = "Xin Qi and Lee, {Sang Hyeup} and Juyoung Yoon and Lee, {Yoon Sik}",

note = "Funding Information: We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.",

year = "2004",

month = may,

day = "3",

doi = "10.1016/j.tet.2004.03.064",

language = "English",

volume = "60",

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journal = "Tetrahedron",

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T1 - Synthesis of novel thiol taxoids based on the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III

T2 - Both the syn and anti 10-deacetyl-2′-deoxy-2′-mercaptopaclitaxels

AU - Qi, Xin

AU - Lee, Sang Hyeup

AU - Yoon, Juyoung

AU - Lee, Yoon Sik

N1 - Funding Information: We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.

PY - 2004/5/3

Y1 - 2004/5/3

N2 - Two new kinds of docetaxel compound, with a mercapto group instead of the hydroxyl on the C13 side chain (both syn and anti), via the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III route, were synthesized. The uses of trans and cis oxazoline compounds, and their stereoselective ring-opening reactions with thiolacetic acid, were proved to be key steps.

AB - Two new kinds of docetaxel compound, with a mercapto group instead of the hydroxyl on the C13 side chain (both syn and anti), via the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III route, were synthesized. The uses of trans and cis oxazoline compounds, and their stereoselective ring-opening reactions with thiolacetic acid, were proved to be key steps.

KW - Mercapto taxoid

KW - Oxazoline

KW - Taxol

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U2 - 10.1016/j.tet.2004.03.064

DO - 10.1016/j.tet.2004.03.064

M3 - Article

AN - SCOPUS:1942471997

SN - 0040-4020

VL - 60

SP - 4133

EP - 4138

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Synthesis of novel thiol taxoids based on the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III: Both the syn and anti 10-deacetyl-2′-deoxy-2′-mercaptopaclitaxels

Abstract

Bibliographical note

Keywords

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