Stereoselective Total Synthesis of Myriocin Using Rhodium(II)-Catalyzed C-H Amination Followed by Alkylation

Hisanori Nambu; Narumi Noda; Wenqi Niu; Tomoya Fujiwara; Takayuki Yakura

doi:10.1002/ajoc.201500318

Stereoselective Total Synthesis of Myriocin Using Rhodium(II)-Catalyzed C-H Amination Followed by Alkylation

Hisanori Nambu, Narumi Noda, Wenqi Niu, Tomoya Fujiwara, Takayuki Yakura^*

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

17 被引用数 (Scopus)

抄録

The stereoselective total synthesis of myriocin was achieved by using the Du Bois Rh^II-catalyzed C-H amination of sulfamate 6, derived from diethyl l-tartrate, and a subsequent alkylation. The reaction of sulfamate 6 with PhI(OAc)₂ and MgO in the presence of Rh₂(OAc)₄ gave an oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of the N,O-acetal with vinylmagnesium bromide in the presence of ZnCl₂ proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. This route includes the first application of the Du Bois procedure for the construction of a quaternary chiral center.

本文言語	英語
ページ（範囲）	1246-1249
ページ数	4
ジャーナル	Asian Journal of Organic Chemistry
巻	4
号	11
DOI	https://doi.org/10.1002/ajoc.201500318
出版ステータス	出版済み - 2015/11

ASJC Scopus 主題領域

有機化学

文献へのアクセス

10.1002/ajoc.201500318

引用スタイル

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title = "Stereoselective Total Synthesis of Myriocin Using Rhodium(II)-Catalyzed C-H Amination Followed by Alkylation",

abstract = "The stereoselective total synthesis of myriocin was achieved by using the Du Bois RhII-catalyzed C-H amination of sulfamate 6, derived from diethyl l-tartrate, and a subsequent alkylation. The reaction of sulfamate 6 with PhI(OAc)2 and MgO in the presence of Rh2(OAc)4 gave an oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of the N,O-acetal with vinylmagnesium bromide in the presence of ZnCl2 proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. This route includes the first application of the Du Bois procedure for the construction of a quaternary chiral center.",

keywords = "Alkylation, C-H amination, Myriocin, Rhodium, Total synthesis",

author = "Hisanori Nambu and Narumi Noda and Wenqi Niu and Tomoya Fujiwara and Takayuki Yakura",

note = "Publisher Copyright: & Co. KGaA, Weinheim.",

year = "2015",

month = nov,

doi = "10.1002/ajoc.201500318",

language = "英語",

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pages = "1246--1249",

journal = "Asian Journal of Organic Chemistry",

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T1 - Stereoselective Total Synthesis of Myriocin Using Rhodium(II)-Catalyzed C-H Amination Followed by Alkylation

AU - Nambu, Hisanori

AU - Noda, Narumi

AU - Niu, Wenqi

AU - Fujiwara, Tomoya

AU - Yakura, Takayuki

N1 - Publisher Copyright: & Co. KGaA, Weinheim.

PY - 2015/11

Y1 - 2015/11

N2 - The stereoselective total synthesis of myriocin was achieved by using the Du Bois RhII-catalyzed C-H amination of sulfamate 6, derived from diethyl l-tartrate, and a subsequent alkylation. The reaction of sulfamate 6 with PhI(OAc)2 and MgO in the presence of Rh2(OAc)4 gave an oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of the N,O-acetal with vinylmagnesium bromide in the presence of ZnCl2 proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. This route includes the first application of the Du Bois procedure for the construction of a quaternary chiral center.

AB - The stereoselective total synthesis of myriocin was achieved by using the Du Bois RhII-catalyzed C-H amination of sulfamate 6, derived from diethyl l-tartrate, and a subsequent alkylation. The reaction of sulfamate 6 with PhI(OAc)2 and MgO in the presence of Rh2(OAc)4 gave an oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of the N,O-acetal with vinylmagnesium bromide in the presence of ZnCl2 proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. This route includes the first application of the Du Bois procedure for the construction of a quaternary chiral center.

KW - Alkylation

KW - C-H amination

KW - Myriocin

KW - Rhodium

KW - Total synthesis

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U2 - 10.1002/ajoc.201500318

DO - 10.1002/ajoc.201500318

M3 - 学術論文

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SN - 2193-5807

VL - 4

SP - 1246

EP - 1249

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 11

ER -

Stereoselective Total Synthesis of Myriocin Using Rhodium(II)-Catalyzed C-H Amination Followed by Alkylation

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