The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)

Kuniaki Tatsuta; Sonoko Tokishita; Tomohiro Fukuda; Takaaki Kano; Tadaaki Komiya; Seijiro Hosokawa

doi:10.1016/j.tetlet.2010.12.061

The first total synthesis and structural determination of antibiotics K1115 B₁s (alnumycins)

Kuniaki Tatsuta, Sonoko Tokishita, Tomohiro Fukuda, Takaaki Kano, Tadaaki Komiya, Seijiro Hosokawa

School of Advanced Science and Engineering

Research output: Contribution to journal › Article

14 Citations (Scopus)

Abstract

K1115 B₁, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B₁ by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of ¹H NMR spectra and optical rotations made it clear that the absolute structures of K1115 B _1α (the major isomer) and K1115 B_1β (the minor isomer) were (1R, 17S)- and (1R, 17R)-configurations, respectively. The optical rotations of the stereoisomers revealed that alnumycin, reported as the identical structure with K1115 B₁, might be another mixture of stereoisomers.

Original language	English
Pages (from-to)	983-986
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2010.12.061
Publication status	Published - 2011 Mar 2

Keywords

Alnumycin
BE-41956A
K1115 B
Michael-Dieckmann type condensation
Structural determination
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Tatsuta, K., Tokishita, S., Fukuda, T., Kano, T., Komiya, T., & Hosokawa, S. (2011). The first total synthesis and structural determination of antibiotics K1115 B₁s (alnumycins). Tetrahedron Letters, 52(9), 983-986. https://doi.org/10.1016/j.tetlet.2010.12.061

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AU - Tokishita, Sonoko

AU - Fukuda, Tomohiro

AU - Kano, Takaaki

AU - Komiya, Tadaaki

AU - Hosokawa, Seijiro

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AB - K1115 B1, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B1 by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of 1H NMR spectra and optical rotations made it clear that the absolute structures of K1115 B 1α (the major isomer) and K1115 B1β (the minor isomer) were (1R, 17S)- and (1R, 17R)-configurations, respectively. The optical rotations of the stereoisomers revealed that alnumycin, reported as the identical structure with K1115 B1, might be another mixture of stereoisomers.

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