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

^*Corresponding author for this work

School of Advanced Science and Engineering

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

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

Access to Document

10.1016/j.tetlet.2010.12.061

Cite this

@article{7f70656c7bc74f8aa997c63df1516c66,

title = "The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)",

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 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.",

keywords = "Alnumycin, BE-41956A, K1115 B, Michael-Dieckmann type condensation, Structural determination, Total synthesis",

author = "Kuniaki Tatsuta and Sonoko Tokishita and Tomohiro Fukuda and Takaaki Kano and Tadaaki Komiya and Seijiro Hosokawa",

note = "Funding Information: Authors thank Eisai Co., Ltd for giving NMR spectra of the natural product and Streptomyces griseorubiginosus (Mer-K1115) strain. Authors also thank Dr. Yoshikazu Takahashi of Microbial Chemistry Research Center for fermentation of the strain. Additionally, authors thanks Mr. Hiroomi Ogino, Mr. Tatsuya Nakamura, and Dr. Yoshikazu Suzuki for the preliminary studies. Authors are grateful for financial support to GCOE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright}, and the Ministry of Education, Culture, Sports, Science and Technology (MEXT). ",

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AU - Tatsuta, Kuniaki

AU - Tokishita, Sonoko

AU - Fukuda, Tomohiro

AU - Kano, Takaaki

AU - Komiya, Tadaaki

AU - Hosokawa, Seijiro

N1 - Funding Information: Authors thank Eisai Co., Ltd for giving NMR spectra of the natural product and Streptomyces griseorubiginosus (Mer-K1115) strain. Authors also thank Dr. Yoshikazu Takahashi of Microbial Chemistry Research Center for fermentation of the strain. Additionally, authors thanks Mr. Hiroomi Ogino, Mr. Tatsuya Nakamura, and Dr. Yoshikazu Suzuki for the preliminary studies. Authors are grateful for financial support to GCOE program ‘Center for Practical Chemical Wisdom’, and the Ministry of Education, Culture, Sports, Science and Technology (MEXT).

PY - 2011/3/2

Y1 - 2011/3/2

N2 - 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.

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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KW - Total synthesis

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