Abstract
A new annelation procedure has been developed in a model system to introduce the cyclohexene ring of guanacastepene. Cyclohexenone 16 is prepared by sequential methylation and alkylation with allylic iodide 15 . One-pot epoxidation, protodesilylation and hydrolysis of the THP forms dione 19 , which cyclizes with NaOMe to 24 in 57% overall yield. Reduction, Mitsunobu inversion, and selective oxidation of the primary alcohol forms model 29 . Phenyldimethylsilyl allylic iodide 36 is easier to make and more stable than trimethylsilyl allylic iodide 6 used by Stork.
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