Total synthesis of (12R)- and (12S)-12-hydroxymonocerins: stereoselective oxylactonization using a chiral hypervalent iodine(iii) species?

RSC Advances Pub Date: 2013-07-24 DOI: 10.1039/C3RA43230K

Abstract

The first total syntheses of (12R)- and (12S)-12-hydroxymonocerins are described. The oxolane-fused isochroman-1-one framework is stereoselectively constructed via a double oxy-cyclization using a lactate-based chiral hypervalent iodine reagent. A catalytic variant of the double oxy-cyclization is also demonstrated using a chiral iodoarene as the precatalyst and m-CPBA as the co-oxidant.

Graphical abstract: Total synthesis of (12R)- and (12S)-12-hydroxymonocerins: stereoselective oxylactonization using a chiral hypervalent iodine(iii) species
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