Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

Yasuaki Nakayama; Yuichiro Maeda; Naoto Hama; Takaaki Satou; Noritaka Chida

doi:10.1055/s-0035-1561948

Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

Yasuaki Nakayama, Yuichiro Maeda, Naoto Hama, Takaaki Satou, Noritaka Chida

Department of Applied Chemistry

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

12 Citations (Scopus)

Abstract

The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

Original language	English
Journal	Synthesis (Germany)
DOIs	https://doi.org/10.1055/s-0035-1561948
Publication status	Accepted/In press - 2016 Feb 23

Keywords

alkaloid
allylic compound
diol
sigmatropic rearrangement
total synthesis

ASJC Scopus subject areas

Organic Chemistry
Catalysis

Access to Document

10.1055/s-0035-1561948

Fingerprint Dive into the research topics of 'Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement'. Together they form a unique fingerprint.

Cite this

@article{a55006f59d6f4184ae39ab159b998c31,

title = "Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement",

abstract = "The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.",

keywords = "alkaloid, allylic compound, diol, sigmatropic rearrangement, total synthesis",

author = "Yasuaki Nakayama and Yuichiro Maeda and Naoto Hama and Takaaki Satou and Noritaka Chida",

year = "2016",

month = feb,

day = "23",

doi = "10.1055/s-0035-1561948",

language = "English",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

}

TY - JOUR

T1 - Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

AU - Nakayama, Yasuaki

AU - Maeda, Yuichiro

AU - Hama, Naoto

AU - Satou, Takaaki

AU - Chida, Noritaka

PY - 2016/2/23

Y1 - 2016/2/23

N2 - The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

AB - The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

KW - alkaloid

KW - allylic compound

KW - diol

KW - sigmatropic rearrangement

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84977989260&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84977989260&partnerID=8YFLogxK

U2 - 10.1055/s-0035-1561948

DO - 10.1055/s-0035-1561948

M3 - Article

AN - SCOPUS:84977989260

JO - Synthesis (Germany)

JF - Synthesis (Germany)

SN - 0039-7881

ER -