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

医学部

研究成果: Article › 査読

23 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	1943-1947
ページ数	5
ジャーナル	Tetrahedron Letters
巻	49
号	12
DOI	https://doi.org/10.1016/j.tetlet.2008.01.105
出版ステータス	Published - 2008 3月 17

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tetlet.2008.01.105

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@article{61887f0cc5c24bc5820856b783dbcc0e,

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. ",

year = "2008",

month = mar,

day = "17",

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

language = "English",

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journal = "Tetrahedron Letters",

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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

UR - https://www.scopus.com/pages/publications/39149126391

UR - https://www.scopus.com/pages/publications/39149126391#tab=citedBy

U2 - 10.1016/j.tetlet.2008.01.105

DO - 10.1016/j.tetlet.2008.01.105

M3 - Article

AN - SCOPUS:39149126391

SN - 0040-4039

VL - 49

SP - 1943

EP - 1947

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Total synthesis of mycestericin A

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