Synthesis 2016; 48(05): 765-771
DOI: 10.1055/s-0035-1561114
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective­ Oxypalladation

Yuji Kurogome
a   Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
,
Yasunao Hattori
b   Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan
,
Hidefumi Makabe*
a   Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
c   Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan   Email: makabeh@shinshu-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 12 November 2015

Accepted after revision: 04 December 2015

Publication Date:
04 January 2016 (online)


Abstract

Stereoselective synthesis of decytospolide A and B and their C-3 epimers, which have a 2,6-cis-tetrahydropyran ring, has been achieved in high stereoselectivity and yield. The oxypalladation of single diastereomers of 6-(benzyloxy)-7-hydroxydodec-2-enyl 2-naphthoates was optimized to give products with a 2,6-cis-tetrahydropyran ring with high diastereoselectivity and yield.

Supporting Information