Stereoselective Approach to the Core Structure of (+)-Phainanoid A via Strategically Engineered Cascade Polyene Cyclization

초록

Stereoselective synthesis of 3b and its cascade polyene cyclization to 18b have been described. Acyclic polyene 3b was prepared from allyl bromide 4 and 1,3-dithiane 5, and intermediates 4 and 5 were synthesized from the commercially available geraniol (6) and cyclopenten-2-one (8), respectively, using enantioselective reduction of ketone, Johnson-Claisen rearrangement, and the Suzuki reaction as key steps. Au(I)-mediated diastereoselective polyene cyclization of 3b efficiently afforded tetracyclic compound 18b.

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