Syntheses of new fluorine-containing taxoids by means of β-lactam synthon method

Iwao Ojima; Scott D. Kuduk; John C. Slater; Rayomand H. Gimi; Chung Ming Sun

doi:10.1016/0040-4020(95)00865-6

Syntheses of new fluorine-containing taxoids by means of β-lactam synthon method

Iwao Ojima
, Scott D. Kuduk
, John C. Slater
, Rayomand H. Gimi
, Chung Ming Sun

Chemistry

Stony Brook University

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

51 Scopus citations

Abstract

A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,45)-1-acyl-β-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14β-hydroxy-10-deacetylbaccatin III as the key step (β-Lactam Synthon Method). (3R,4S)-1-Acyl-β-lactams are prepared through efficient chiral ester enolate - imine cyclocondensation.

Original language	English
Pages (from-to)	209-224
Number of pages	16
Journal	Tetrahedron
Volume	52
Issue number	1
DOIs	https://doi.org/10.1016/0040-4020(95)00865-6
State	Published - 1996

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title = "Syntheses of new fluorine-containing taxoids by means of β-lactam synthon method",

abstract = "A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,45)-1-acyl-β-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14β-hydroxy-10-deacetylbaccatin III as the key step (β-Lactam Synthon Method). (3R,4S)-1-Acyl-β-lactams are prepared through efficient chiral ester enolate - imine cyclocondensation.",

author = "Iwao Ojima and Kuduk, \{Scott D.\} and Slater, \{John C.\} and Gimi, \{Rayomand H.\} and Sun, \{Chung Ming\}",

year = "1996",

doi = "10.1016/0040-4020(95)00865-6",

language = "English",

volume = "52",

pages = "209--224",

journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Syntheses of new fluorine-containing taxoids by means of β-lactam synthon method

AU - Ojima, Iwao

AU - Kuduk, Scott D.

AU - Slater, John C.

AU - Gimi, Rayomand H.

AU - Sun, Chung Ming

PY - 1996

Y1 - 1996

N2 - A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,45)-1-acyl-β-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14β-hydroxy-10-deacetylbaccatin III as the key step (β-Lactam Synthon Method). (3R,4S)-1-Acyl-β-lactams are prepared through efficient chiral ester enolate - imine cyclocondensation.

AB - A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,45)-1-acyl-β-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14β-hydroxy-10-deacetylbaccatin III as the key step (β-Lactam Synthon Method). (3R,4S)-1-Acyl-β-lactams are prepared through efficient chiral ester enolate - imine cyclocondensation.

UR - https://www.scopus.com/pages/publications/0029655687

U2 - 10.1016/0040-4020(95)00865-6

DO - 10.1016/0040-4020(95)00865-6

M3 - Article

AN - SCOPUS:0029655687

SN - 0040-4020

VL - 52

SP - 209

EP - 224

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Syntheses of new fluorine-containing taxoids by means of β-lactam synthon method

Abstract

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