Abstract
The (R)-7-pentylthiocaprolactam 1, a formal precursor of (−)-perhydrohistrionicotoxin 2 is synthetized in four steps using asymmetric alkylation of cyclohexanone. Metalation and alkylation of (R)-imine 3 afford after hydrolysis (R)-2-pentylcyclohexanone 4 with high stereoselectivity (e.e.=78%). The Beckmann type rearrangement of the optically enriched ketone 4 proceeds without racemization. The resulting 7-pentylcaprolactam 6 was transformed in two steps to the (R)-benzylthiolactam which was purified by recrystallization to give optically pure compound 1 (e.e.>95%).
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