On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB: A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments

Shawn J. Stachel; Mark D. Chappell; Chul Bom Lee; Samuel J. Danishefsky; Ting Chao Chou; Lifeng He; Susan B. Horwitz

doi:10.1021/ol005932m

On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB: A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments

Shawn J. Stachel, Mark D. Chappell, Chul Bom Lee, Samuel J. Danishefsky, Ting Chao Chou, Lifeng He, Susan B. Horwitz

Molecular Pharmacology

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30 Scopus citations

Abstract

(Equation Presented) The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothilone B, are described. A Mitsunobu inversion was utilized for elaboration of pre-epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented.

Original language	English (US)
Pages (from-to)	1637-1639
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	11
DOIs	https://doi.org/10.1021/ol005932m
State	Published - Jun 1 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB: A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments",

abstract = "(Equation Presented) The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothilone B, are described. A Mitsunobu inversion was utilized for elaboration of pre-epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented.",

author = "Stachel, {Shawn J.} and Chappell, {Mark D.} and Lee, {Chul Bom} and Danishefsky, {Samuel J.} and Chou, {Ting Chao} and Lifeng He and Horwitz, {Susan B.}",

year = "2000",

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doi = "10.1021/ol005932m",

language = "English (US)",

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journal = "Organic Letters",

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TY - JOUR

T1 - On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB

T2 - A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments

AU - Stachel, Shawn J.

AU - Chappell, Mark D.

AU - Lee, Chul Bom

AU - Danishefsky, Samuel J.

AU - Chou, Ting Chao

AU - He, Lifeng

AU - Horwitz, Susan B.

PY - 2000/6/1

Y1 - 2000/6/1

N2 - (Equation Presented) The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothilone B, are described. A Mitsunobu inversion was utilized for elaboration of pre-epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented.

AB - (Equation Presented) The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothilone B, are described. A Mitsunobu inversion was utilized for elaboration of pre-epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented.

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U2 - 10.1021/ol005932m

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SN - 1523-7060

VL - 2

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EP - 1639

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB: A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments

Abstract

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