Synthesis 2016; 48(11): 1647-1654
DOI: 10.1055/s-0035-1561948
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Yasuaki Nakayama
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   Email: takaakis@applc.keio.ac.jp   Email: chida@applc.keio.ac.jp
,
Yuichiro Maeda
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   Email: takaakis@applc.keio.ac.jp   Email: chida@applc.keio.ac.jp
,
Naoto Hama
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   Email: takaakis@applc.keio.ac.jp   Email: chida@applc.keio.ac.jp
,
Takaaki Sato*
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   Email: takaakis@applc.keio.ac.jp   Email: chida@applc.keio.ac.jp
,
Noritaka Chida*
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   Email: takaakis@applc.keio.ac.jp   Email: chida@applc.keio.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 21 January 2016

Accepted after revision: 23 February 2016

Publication Date:
22 March 2016 (online)

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.

Supporting Information

 
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