Total synthesis of (+)-tautomycin

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)13363-13408
Number of pages46
JournalTetrahedron
Volume52
Issue number42
DOIs
Publication statusPublished - 1996 Oct 14
Externally publishedYes

Fingerprint

Esterification
Phosphoprotein Phosphatases
tautomycin
3-hydroxybutanal

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Shimizu, S., Nakamura, S. I., Nakada, M., & Shibasaki, M. (1996). Total synthesis of (+)-tautomycin. Tetrahedron, 52(42), 13363-13408. https://doi.org/10.1016/0040-4020(96)00811-3

Total synthesis of (+)-tautomycin. / Shimizu, Satoshi; Nakamura, Sei Ichi; Nakada, Masahisa; Shibasaki, Masakatsu.

In: Tetrahedron, Vol. 52, No. 42, 14.10.1996, p. 13363-13408.

Research output: Contribution to journalArticle

Shimizu, S, Nakamura, SI, Nakada, M & Shibasaki, M 1996, 'Total synthesis of (+)-tautomycin', Tetrahedron, vol. 52, no. 42, pp. 13363-13408. https://doi.org/10.1016/0040-4020(96)00811-3
Shimizu S, Nakamura SI, Nakada M, Shibasaki M. Total synthesis of (+)-tautomycin. Tetrahedron. 1996 Oct 14;52(42):13363-13408. https://doi.org/10.1016/0040-4020(96)00811-3
Shimizu, Satoshi ; Nakamura, Sei Ichi ; Nakada, Masahisa ; Shibasaki, Masakatsu. / Total synthesis of (+)-tautomycin. In: Tetrahedron. 1996 ; Vol. 52, No. 42. pp. 13363-13408.
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