Stereocontrolled Synthesis of ABC Tricycle of Solanoeclepin A

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

Key words

solanoeclepin A - natural products - radical cyclization - iodo­etherification - enyne metathesis

• References and Notes

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