Diastereodivergent Synthesis of Syn- and Anti-9-Hydroxyhomoisoflavanone and its Application to the Total Syntheses of (+/-)-Homoferrugenone and (+/-)-Portulacanone F

초록

The diastereodivergent synthesis of synand anti-9-hydroxyhomoisoflavanone from various chromones and carbaldehydes is described. The synthetic approaches involving the reductive aldol reaction or the Morita-Baylis-Hillman reaction followed by syn-selective 1,4-reduction provide both diastereomers of beta-hydroxy chroman-4-ones in 51-98% yield with anti (2 : 1-16 : 1 anti/syn) or 22-80% yield with syn (5 : 1-48 : 1 syn/anti) diastereo-selectivity. The ambiguity surrounding the stereochemistry of two 9-hydroxyhomoisoflavanones, homoferrugenone and portulacanone F was elucidated via the first total syntheses.

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