Synlett 2017; 28(17): 2340-2344
DOI: 10.1055/s-0036-1590970
letter
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene–Claisen Rearrangement

Kenji Matsumoto*a, Naoyuki Mizushinab, Masahiro Yoshidaa, Mitsuru Shindo*c
  • aFaculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihama-Boji, Yamashiro-cho, Tokushima 770-8514, Japan   Email: kmatsumoto@ph.bunri-u.ac.jp
  • bInterdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan
  • cInstitute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan   Email: shindo@cm.kyushu-u.ac.jp
This work was partially supported by JSPS KAKENHI (grant numbers JP16H01157 and JP26293004), the Science and Technology Research Promotion Program for Agriculture, Forestry, Fisheries, and Food Industry (M. S.), the NOVARTIS Foundation for the Promotion of Science, the Kurata Memorial Hitachi Science and Technology Foundation (K. M.), and the Cooperative Research Program of the Network Joint Research Center for Materials and Devices
Further Information

Publication History

Received: 28 April 2017

Accepted after revision: 03 July 2017

Publication Date:
27 July 2017 (eFirst)

Abstract

We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene–Claisen rearrangement. The Claisen rearrangement of anti-allenyl alcohols provided (1E,3Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels–Alder reactions are described.

Supporting Information