Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity.

Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Research Abstract Details 

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Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Abstract Text:

Hiroshi Araki,Munenori Inoue,Takeyuki Suzuki,Takao Yamori,Michiaki Kohno,Kazuhiro Watanabe,Hideki Abe,Tadashi Katoh,Hiroshi Araki,Munenori Inoue,Takeyuki Suzuki,Takao Yamori,Michiaki Kohno,Kazuhiro Watanabe,Hideki Abe,Tadashi Katoh,Hiroshi Araki,Munenori Inoue,Takeyuki Suzuki,Takao Yamori,Michiaki Kohno,Kazuhiro Watanabe,Hideki Abe,Tadashi Katoh,

Enantioselective total synthesis of (+)-ottelione A (1) and (-)-ottelione B (2), novel and potent antitumor agents from a freshwater plant, and (+)-3-epi-ottelione A (3), the earlier proposed stereostructure of 1, was efficiently achieved starting from the known tricyclic compound 10. The synthesis involved the following key steps: i) coupling reactions of aldehydes 8 and 9 with the aromatic portion 7 (8+7-->15 and 9+7-->27), ii) base-induced hemiacetal-opening/epimerization reactions of the cyclic hemiacetals 6 and 27 (6-->17 and 27 a-->26 a), and iii) Corey-Winter's reductive olefination of the cyclic thiocarbonates 21 and 36 (21-->22 and 36-->37). The present total synthesis fully established the absolute configuration of these natural products. The cell growth inhibition profile, COMPARE analysis, and tubulin inhibitory assay of (+)-3-epi-ottelione A (3) and its O-acetyl derivative 24 demonstrated that these unnatural substances could be prominent lead compounds for the development of anticancer agents with a novel mode of action.

Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Publishing Authors By Initials

H Araki,M Inoue,T Suzuki,T Yamori,M Kohno,K Watanabe,H Abe,T Katoh,H Araki,M Inoue,T Suzuki,T Yamori,M Kohno,K Watanabe,H Abe,T Katoh,H Araki,M Inoue,T Suzuki,T Yamori,M Kohno,K Watanabe,H Abe,T Katoh,

For similar macromolecular substances: polymers: biopolymers: microtubule proteins: tubulin research abstracts see: macromolecular substances: polymers: biopolymers: microtubule proteins: tubulin research

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Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)

VOLUME: 13

Page Numbers: 9866-81

Journal Abbreviation:

ISSN: 0947-6539

DAY: 8

MONTH: 02

YEAR: 2007

Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Information

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LANGUAGE: eng

NlmUniqueID: 9513783

Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Keywords Mesh Terms:

KEYWORDS: Tubulin

MESH TERMS: metabolism

Chemical & Substance for Abstract: Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Information

Substance Name: ottelione B

Registry Number: 0

Grant and Affiliation Information for Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity.

AFFILIATION: Department of Electronic Chemistry, Tokyo Institute of Technology, Nagatsuta, Yokohama, Japan.

Country: Germany

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MEDLINETA: Chemistry

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