Total synthesis of (+)-tautomycin

Satoshi Shimizu; Sei Ichi Nakamura; Masahisa Nakada; Masakatsu Shibasaki

doi:10.1016/0040-4020(96)00811-3

Total synthesis of (+)-tautomycin

Satoshi Shimizu, Sei Ichi Nakamura, Masahisa Nakada, Masakatsu Shibasaki^*

^*Corresponding author for this work

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

31 Citations (Scopus)

Abstract

A convergent stereocontrolled total synthesis of (+)-tautomycin (1), a specific inhibitor of protein serine/threonine phosphatases, has been achieved through an esterification of the C₁.-C₇. fragment A'74 with the C₁-C₂₆ fragment B'76 by a modified Yamaguchi method and an aldol reaction of the C₁₇-C₂₆ fragment C 5 with the C₁-C₁₆ fragment D 6 using LDA as key steps. The fragments 5 and 6 have been constructed in a stereocontrolled manner, respectively.

Original language	English
Pages (from-to)	13363-13408
Number of pages	46
Journal	Tetrahedron
Volume	52
Issue number	42
DOIs	https://doi.org/10.1016/0040-4020(96)00811-3
Publication status	Published - 1996 Oct 14
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4020(96)00811-3

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AU - Shimizu, Satoshi

AU - Nakamura, Sei Ichi

AU - Nakada, Masahisa

AU - Shibasaki, Masakatsu

PY - 1996/10/14

Y1 - 1996/10/14

N2 - A convergent stereocontrolled total synthesis of (+)-tautomycin (1), a specific inhibitor of protein serine/threonine phosphatases, has been achieved through an esterification of the C1.-C7. fragment A'74 with the C1-C26 fragment B'76 by a modified Yamaguchi method and an aldol reaction of the C17-C26 fragment C 5 with the C1-C16 fragment D 6 using LDA as key steps. The fragments 5 and 6 have been constructed in a stereocontrolled manner, respectively.

AB - A convergent stereocontrolled total synthesis of (+)-tautomycin (1), a specific inhibitor of protein serine/threonine phosphatases, has been achieved through an esterification of the C1.-C7. fragment A'74 with the C1-C26 fragment B'76 by a modified Yamaguchi method and an aldol reaction of the C17-C26 fragment C 5 with the C1-C16 fragment D 6 using LDA as key steps. The fragments 5 and 6 have been constructed in a stereocontrolled manner, respectively.

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JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

Total synthesis of (+)-tautomycin

Abstract

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