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Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade
Misaki Kawamoto1, Shuntaro Sato1, Masaru Enomoto1
1Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki-Aza-Aoba , Aoba-ku , Sendai 980-0845 , Japan.
Abstract:
A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.
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