Synthesis of (±)-Pterocarpin and Its Thia- and Aza-Analogues in a Modular Manner

Abstract

Syntheses of racemic pterocarpin, its thia- and aza-pterocarpin have been achieved in a modular manner using sesamol iodide, diethyl malonate and 3-methoxyphenol, 3-methoxythiophenol and N-tosyl-3-methoxyaniline as building blocks. Copper-mediated Hurtley coupling, Mitsunobu reaction, IBX-mediated oxidation, Pinnick oxidation, and intramolecular Friedel–Crafts acylation have been successfully exploited in the synthesis.

Key words

pterocarpin synthesis - thia-pterocarpin synthesis - aza-pterocarpin synthesis - pterocarpan synthesis - isoflavanone synthesis

• References and Notes

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