Synthesis of dysiherbaine analogue

Muneo Shoji; Kaoru Shiohara; Masato Oikawa; Ryuichi Sakai; Makoto Sasaki

doi:10.1016/j.tetlet.2005.06.093

Synthesis of dysiherbaine analogue

Muneo Shoji, Kaoru Shiohara, Masato Oikawa, Ryuichi Sakai, Makoto Sasaki

LIF - Molecular and Chemical Life Science

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

17 Citations (Scopus)

Abstract

Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C₆ stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided.

Original language	English
Pages (from-to)	5559-5562
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2005.06.093
Publication status	Published - 2005 Aug 15

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.06.093

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title = "Synthesis of dysiherbaine analogue",

abstract = "Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C6 stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided.",

author = "Muneo Shoji and Kaoru Shiohara and Masato Oikawa and Ryuichi Sakai and Makoto Sasaki",

note = "Funding Information: This work was financially supported by Yamada Science Foundation and a Grant-in-Aid for Scientific Research on Priority Area {\textquoteleft}Creation of Biologically Functional Molecules{\textquoteright} from the Ministry of Education, Science, Sports, Culture and Technology, Japan. ",

year = "2005",

month = aug,

day = "15",

doi = "10.1016/j.tetlet.2005.06.093",

language = "English",

volume = "46",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Synthesis of dysiherbaine analogue

AU - Shoji, Muneo

AU - Shiohara, Kaoru

AU - Oikawa, Masato

AU - Sakai, Ryuichi

AU - Sasaki, Makoto

N1 - Funding Information: This work was financially supported by Yamada Science Foundation and a Grant-in-Aid for Scientific Research on Priority Area ‘Creation of Biologically Functional Molecules’ from the Ministry of Education, Science, Sports, Culture and Technology, Japan.

PY - 2005/8/15

Y1 - 2005/8/15

N2 - Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C6 stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided.

AB - Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C6 stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided.

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DO - 10.1016/j.tetlet.2005.06.093

M3 - Article

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EP - 5562

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 33

ER -

Synthesis of dysiherbaine analogue

Abstract

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