Synlett 2015; 26(07): 965-969
DOI: 10.1055/s-0034-1380399
letter
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of ABC Tricycle of Solanoeclepin A

Masaatsu Adachi*
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: madachi@agr.nagoya-u.ac.jp   Email: nisikawa@agr.nagoya-u.ac.jp
,
Mai Torii
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: madachi@agr.nagoya-u.ac.jp   Email: nisikawa@agr.nagoya-u.ac.jp
,
Toshio Nishikawa*
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: madachi@agr.nagoya-u.ac.jp   Email: nisikawa@agr.nagoya-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 04 December 2014

Accepted after revision: 22 January 2015

Publication Date:
03 March 2015 (online)


Dedicated to Professor Minoru Isobe on the occasion of his 70th birthday

Abstract

A tricyclic compound possessing oxabicyclo[2.2.1]heptane and seven-membered ring of solanoeclepin A, the most active hatching agent of potato cyst nematode, was synthesized from d-pantolactone. The synthesis features a tin-mediated 6-exo-trig radical cyclization followed by iodoetherification and ring-closing enyne metathesis.

Supporting Information

 
  • References and Notes

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