Amino acids and peptides. XIX. Synthetic study of optically active carene skeleton from .ALPHA.-amino acid. Total synthesis of (+)-2-carene.

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Abstract
For a total synthesis of the optically active carene congeners from optically active α-amino acids, several attempts were made on intramolecular cyclization of 2-cyclohexenyl esters of α-substituted α-diazoacetic acid (III) which were derived from the corresponding amino acid esters. One of the optically active diastereoisomers (X) which was obtained by separation of 2-cyclohexenyl L-alaninate was diazotized with isoamylnitrite and then cyclized using Cu powder as a catalyst to afford the optically active lactone (XIX). XIX was then converted into the key intermediate (XXI) having the bicyclo[4, 1, 0]heptane ring system, from which (+)-2-carene was synthesized.

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