Total synthesis of mycestericin A

Hideyuki Sato; Kazuya Sato; Masatoshi Iida; Hiroyoshi Yamanaka; Takeshi Oishi; Noritaka Chida

doi:10.1016/j.tetlet.2008.01.105

Total synthesis of mycestericin A

Hideyuki Sato, Kazuya Sato, Masatoshi Iida, Hiroyoshi Yamanaka, Takeshi Oishi, Noritaka Chida

School of Medicine

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

19 Citations (Scopus)

Abstract

The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1.

Original language	English
Pages (from-to)	1943-1947
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2008.01.105
Publication status	Published - 2008 Mar 17

Keywords

Immunosuppressant
Mycestericin A
Negishi coupling
Overman rearrangement
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.01.105

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title = "Total synthesis of mycestericin A",

abstract = "The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1.",

keywords = "Immunosuppressant, Mycestericin A, Negishi coupling, Overman rearrangement, Total synthesis",

author = "Hideyuki Sato and Kazuya Sato and Masatoshi Iida and Hiroyoshi Yamanaka and Takeshi Oishi and Noritaka Chida",

note = "Funding Information: This work was supported in part by Grant-in-Aid for the 21st Century COE Program {\textquoteleft}Keio Life Conjugate Chemistry{\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. ",

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doi = "10.1016/j.tetlet.2008.01.105",

language = "English",

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T1 - Total synthesis of mycestericin A

AU - Sato, Hideyuki

AU - Sato, Kazuya

AU - Iida, Masatoshi

AU - Yamanaka, Hiroyoshi

AU - Oishi, Takeshi

AU - Chida, Noritaka

N1 - Funding Information: This work was supported in part by Grant-in-Aid for the 21st Century COE Program ‘Keio Life Conjugate Chemistry’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2008/3/17

Y1 - 2008/3/17

N2 - The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1.

AB - The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1.

KW - Immunosuppressant

KW - Mycestericin A

KW - Negishi coupling

KW - Overman rearrangement

KW - Total synthesis

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DO - 10.1016/j.tetlet.2008.01.105

M3 - Article

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SN - 0040-4039

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SP - 1943

EP - 1947

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Total synthesis of mycestericin A

Abstract

Keywords

ASJC Scopus subject areas

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