Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol.

ABSTRACT

[figure see text] Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.