Total synthesis of attenols A and B

Keisuke Araki; Kiyotake Suenaga; Tetsuya Sengoku; Daisuke Uemura

doi:10.1016/S0040-4020(02)00056-X

Total synthesis of attenols A and B

Keisuke Araki, Kiyotake Suenaga, Tetsuya Sengoku, Daisuke Uemura

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

43 Citations (Scopus)

Abstract

The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.

Original language	English
Pages (from-to)	1983-1995
Number of pages	13
Journal	Tetrahedron
Volume	58
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4020(02)00056-X
Publication status	Published - 2002 Mar 4
Externally published	Yes

Keywords

Biological studies
Diastereoselective hydroboration
Enantioselective synthesis
Semigram scale
Stereochemistry of spiro acetal ring

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/S0040-4020(02)00056-X

Cite this

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title = "Total synthesis of attenols A and B",

abstract = "The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.",

keywords = "Biological studies, Diastereoselective hydroboration, Enantioselective synthesis, Semigram scale, Stereochemistry of spiro acetal ring",

author = "Keisuke Araki and Kiyotake Suenaga and Tetsuya Sengoku and Daisuke Uemura",

note = "Funding Information: This work was supported in part by Wako Pure Chemical Industries Ltd, by Banyu Pharmaceutical Co., Ltd, and by Grants-in-Aid (Nos. 11558079 and 12045235) for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan. We thank Dr T. Yamori (Screening Committee of New Anticancer Agents supported by a Grant-in Aid for Scientific Research on Priority Area {\textquoteleft}Cancer{\textquoteright} from the Ministry of Education, Science, Sports, and Culture, Japan) for help with screening the human cancer cell line panel.",

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month = mar,

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doi = "10.1016/S0040-4020(02)00056-X",

language = "English",

volume = "58",

pages = "1983--1995",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

number = "10",

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TY - JOUR

T1 - Total synthesis of attenols A and B

AU - Araki, Keisuke

AU - Suenaga, Kiyotake

AU - Sengoku, Tetsuya

AU - Uemura, Daisuke

N1 - Funding Information: This work was supported in part by Wako Pure Chemical Industries Ltd, by Banyu Pharmaceutical Co., Ltd, and by Grants-in-Aid (Nos. 11558079 and 12045235) for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan. We thank Dr T. Yamori (Screening Committee of New Anticancer Agents supported by a Grant-in Aid for Scientific Research on Priority Area ‘Cancer’ from the Ministry of Education, Science, Sports, and Culture, Japan) for help with screening the human cancer cell line panel.

PY - 2002/3/4

Y1 - 2002/3/4

N2 - The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.

AB - The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.

KW - Biological studies

KW - Diastereoselective hydroboration

KW - Enantioselective synthesis

KW - Semigram scale

KW - Stereochemistry of spiro acetal ring

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U2 - 10.1016/S0040-4020(02)00056-X

DO - 10.1016/S0040-4020(02)00056-X

M3 - Article

AN - SCOPUS:0037017722

SN - 0040-4020

VL - 58

SP - 1983

EP - 1995

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Total synthesis of attenols A and B

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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