Total synthesis of broussonetine F: The orthoamide overman rearrangement of an allylic diol

Naoto Hama; Toshihiro Aoki; Shohei Miwa; Miki Yamazaki; Takaaki Sato; Noritaka Chida

doi:10.1021/ol102856j

Total synthesis of broussonetine F: The orthoamide overman rearrangement of an allylic diol

Naoto Hama, Toshihiro Aoki, Shohei Miwa, Miki Yamazaki, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

41 Citations (Scopus)

Abstract

A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

Original language	English
Pages (from-to)	616-619
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	4
DOIs	https://doi.org/10.1021/ol102856j
Publication status	Published - 2011 Feb 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102856j

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title = "Total synthesis of broussonetine F: The orthoamide overman rearrangement of an allylic diol",

abstract = "A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.",

author = "Naoto Hama and Toshihiro Aoki and Shohei Miwa and Miki Yamazaki and Takaaki Sato and Noritaka Chida",

year = "2011",

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journal = "Organic Letters",

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T1 - Total synthesis of broussonetine F

T2 - The orthoamide overman rearrangement of an allylic diol

AU - Hama, Naoto

AU - Aoki, Toshihiro

AU - Miwa, Shohei

AU - Yamazaki, Miki

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2011/2/18

Y1 - 2011/2/18

N2 - A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

AB - A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

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U2 - 10.1021/ol102856j

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JO - Organic Letters

JF - Organic Letters

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Total synthesis of broussonetine F: The orthoamide overman rearrangement of an allylic diol

Abstract

ASJC Scopus subject areas

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