Total synthesis of stevastelins B3 and C3: Structure confirmation of stevastelin B3 and revision of stevastelin C3

Kazuo Kurosawa; Keigo Matsuura; Noritaka Chida

doi:10.1016/j.tetlet.2004.11.121

Total synthesis of stevastelins B3 and C3: Structure confirmation of stevastelin B3 and revision of stevastelin C3

Kazuo Kurosawa, Keigo Matsuura, Noritaka Chida

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

13 Citations (Scopus)

Abstract

The total synthesis of stevastelin B3, stevastelin C3 and 5-deoxy derivative of stevastelin C3, novel 13-membered cyclic depsipeptides, is described. This study unambiguously confirmed the proposed absolute structure of stevastelin B3, and revealed that the structure of stevastelin C3 is incorrect. The correct structure of stevastelin C3 was established by the total synthesis to be 5-deoxy derivative of the proposed structure.

Original language	English
Pages (from-to)	389-392
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2004.11.121
Publication status	Published - 2005 Jan 17
Externally published	Yes

Keywords

Stevastelin B3
Stevastelin C3
Structure revision
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.11.121

Cite this

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title = "Total synthesis of stevastelins B3 and C3: Structure confirmation of stevastelin B3 and revision of stevastelin C3",

abstract = "The total synthesis of stevastelin B3, stevastelin C3 and 5-deoxy derivative of stevastelin C3, novel 13-membered cyclic depsipeptides, is described. This study unambiguously confirmed the proposed absolute structure of stevastelin B3, and revealed that the structure of stevastelin C3 is incorrect. The correct structure of stevastelin C3 was established by the total synthesis to be 5-deoxy derivative of the proposed structure.",

keywords = "Stevastelin B3, Stevastelin C3, Structure revision, Total synthesis",

author = "Kazuo Kurosawa and Keigo Matsuura and Noritaka Chida",

note = "Funding Information: We thank Dr. T. Nishikiori (Pharmaceutical Group, Nippon Kayaku Co., Ltd, Tokyo, Japan) for providing us with natural stevastelins B3 and C3. This work was supported by Grants-in-Aid for the 21st Century COE program {\textquoteleft}KEIO LCC{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

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doi = "10.1016/j.tetlet.2004.11.121",

language = "English",

volume = "46",

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journal = "Tetrahedron Letters",

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T2 - Structure confirmation of stevastelin B3 and revision of stevastelin C3

AU - Kurosawa, Kazuo

AU - Matsuura, Keigo

AU - Chida, Noritaka

N1 - Funding Information: We thank Dr. T. Nishikiori (Pharmaceutical Group, Nippon Kayaku Co., Ltd, Tokyo, Japan) for providing us with natural stevastelins B3 and C3. This work was supported by Grants-in-Aid for the 21st Century COE program ‘KEIO LCC’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2005/1/17

Y1 - 2005/1/17

N2 - The total synthesis of stevastelin B3, stevastelin C3 and 5-deoxy derivative of stevastelin C3, novel 13-membered cyclic depsipeptides, is described. This study unambiguously confirmed the proposed absolute structure of stevastelin B3, and revealed that the structure of stevastelin C3 is incorrect. The correct structure of stevastelin C3 was established by the total synthesis to be 5-deoxy derivative of the proposed structure.

AB - The total synthesis of stevastelin B3, stevastelin C3 and 5-deoxy derivative of stevastelin C3, novel 13-membered cyclic depsipeptides, is described. This study unambiguously confirmed the proposed absolute structure of stevastelin B3, and revealed that the structure of stevastelin C3 is incorrect. The correct structure of stevastelin C3 was established by the total synthesis to be 5-deoxy derivative of the proposed structure.

KW - Stevastelin B3

KW - Stevastelin C3

KW - Structure revision

KW - Total synthesis

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Total synthesis of stevastelins B3 and C3: Structure confirmation of stevastelin B3 and revision of stevastelin C3

Abstract

Keywords

ASJC Scopus subject areas

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