| Abstract
| - (−)-Siccanin (1), a natural product possessing significant antifungal properties, was synthesizedenantioselectively via a biomimetic route. This synthetic route features two sequential radical cyclizations: a Ti(III)-mediated radical cyclization of epoxyolefin 48 to construct the B-ring, and a Suarez reaction toestablish the tetrahyrofuran ring. Chiral chroman moiety of siccanin was prepared based on our recentdevelopment of the Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol trisubstituted allyl carbonates.Several other members of the siccanin family were also synthesized including siccanochromenes A (2), B(3), E (6), F (7), and the methyl ether of siccanochromene C (55). These studies may shed light on thebiosynthesis of this novel family of compounds.
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