Synthetic studies toward biselides. Part 1: Synthesis of the core carbon framework of biselides A, B, and e using Stille coupling

Yohsuke Satoh; Dai Kawamura; Masashi Yamaura; Yoichi Ikeda; Yumi Ochiai; Ichiro Hayakawa; Hideo Kigoshi

doi:10.1016/j.tetlet.2012.01.020

Synthetic studies toward biselides. Part 1: Synthesis of the core carbon framework of biselides A, B, and e using Stille coupling

Yohsuke Satoh, Dai Kawamura, Masashi Yamaura, Yoichi Ikeda, Yumi Ochiai, Ichiro Hayakawa, Hideo Kigoshi

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

4 Citations (Scopus)

Abstract

Biselides A and B are cytotoxic marine polyketides. We have achieved synthesis of the C-1-C-15 segment of biselides A and B by using Stille coupling and regioselective oxidative cleavage as key steps. Furthermore, we constructed the α,β-unsaturated lactone part of biselide E by using a similar strategy.

Original language	English
Pages (from-to)	1390-1392
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2012.01.020
Publication status	Published - Mar 14 2012
Externally published	Yes

Keywords

Biselides
Polyketides
Regioselective oxidative cleavage
Stille coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.01.020

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Synthetic studies toward biselides. Part 1 : Synthesis of the core carbon framework of biselides A, B, and e using Stille coupling. / Satoh, Yohsuke; Kawamura, Dai; Yamaura, Masashi; Ikeda, Yoichi; Ochiai, Yumi; Hayakawa, Ichiro; Kigoshi, Hideo.

In: Tetrahedron Letters, Vol. 53, No. 11, 14.03.2012, p. 1390-1392.

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

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title = "Synthetic studies toward biselides. Part 1: Synthesis of the core carbon framework of biselides A, B, and e using Stille coupling",

abstract = "Biselides A and B are cytotoxic marine polyketides. We have achieved synthesis of the C-1-C-15 segment of biselides A and B by using Stille coupling and regioselective oxidative cleavage as key steps. Furthermore, we constructed the α,β-unsaturated lactone part of biselide E by using a similar strategy.",

keywords = "Biselides, Polyketides, Regioselective oxidative cleavage, Stille coupling",

author = "Yohsuke Satoh and Dai Kawamura and Masashi Yamaura and Yoichi Ikeda and Yumi Ochiai and Ichiro Hayakawa and Hideo Kigoshi",

note = "Funding Information: This work was supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; by a grant from the Uehara Memorial Foundation (H.K.); and by a grant from the University of Tsukuba, Strategic Initiatives (A), Center for Creation of Functional Materials (CCFM). I.H. thanks The Society of Synthetic Organic Chemistry, Japan (Meiji Seika Award in Synthetic Organic Chemistry, Japan) and the Suntory Institute for Bioorganic Research (SUNBOR GRANT) for financial support. ",

year = "2012",

month = mar,

day = "14",

doi = "10.1016/j.tetlet.2012.01.020",

language = "English",

volume = "53",

pages = "1390--1392",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthetic studies toward biselides. Part 1

T2 - Synthesis of the core carbon framework of biselides A, B, and e using Stille coupling

AU - Satoh, Yohsuke

AU - Kawamura, Dai

AU - Yamaura, Masashi

AU - Ikeda, Yoichi

AU - Ochiai, Yumi

AU - Hayakawa, Ichiro

AU - Kigoshi, Hideo

N1 - Funding Information: This work was supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; by a grant from the Uehara Memorial Foundation (H.K.); and by a grant from the University of Tsukuba, Strategic Initiatives (A), Center for Creation of Functional Materials (CCFM). I.H. thanks The Society of Synthetic Organic Chemistry, Japan (Meiji Seika Award in Synthetic Organic Chemistry, Japan) and the Suntory Institute for Bioorganic Research (SUNBOR GRANT) for financial support.

PY - 2012/3/14

Y1 - 2012/3/14

N2 - Biselides A and B are cytotoxic marine polyketides. We have achieved synthesis of the C-1-C-15 segment of biselides A and B by using Stille coupling and regioselective oxidative cleavage as key steps. Furthermore, we constructed the α,β-unsaturated lactone part of biselide E by using a similar strategy.

AB - Biselides A and B are cytotoxic marine polyketides. We have achieved synthesis of the C-1-C-15 segment of biselides A and B by using Stille coupling and regioselective oxidative cleavage as key steps. Furthermore, we constructed the α,β-unsaturated lactone part of biselide E by using a similar strategy.

KW - Biselides

KW - Polyketides

KW - Regioselective oxidative cleavage

KW - Stille coupling

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U2 - 10.1016/j.tetlet.2012.01.020

DO - 10.1016/j.tetlet.2012.01.020

M3 - Article

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VL - 53

SP - 1390

EP - 1392

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 11

ER -

Synthetic studies toward biselides. Part 1: Synthesis of the core carbon framework of biselides A, B, and e using Stille coupling

Abstract

Keywords

ASJC Scopus subject areas

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