An enantiodivergent route to both enantiomers of P-santalene and epi-p-santalene, constituents of East Indian sandalwood oil, has been developed using a single chiral template.
An efficient synthesis of (S)-5-hydroxymethylbuten-2-olide(1) from D-mannitol has recently been developed by this laboratory.1 In this context, we report here a stereocontrolled enantiodivergent route to both enantiomers of p-santalene2 (26) and epi-P-santalene3 (31), constituents of the prized essential oil of East Indian sandalwood, using (1) as common chiral template.Heating (1) with excess of cyclopentadiene (10.0 equiv.) in a sealed tube (140"C, 9 h) without solvent gave the crystalline CHC13), in 60% yield after removal of a minor amount of isomeric adducts by recrystallization (hexane-ether) . The
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