Amino Acids and Peptides. XIX. Synthetic Study of optically Active Carene Skeleton from α-Amino Acid. Total Synthesis of (+)-2-Carene

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 opti...

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Published inChemical & pharmaceutical bulletin Vol. 23; no. 11; pp. 2539 - 2549
Main Authors YAMADA, SHUNICHI, TAKAMURA, NORIO, MIZOGUCHI, TOMISHIGE
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 1975
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Summary: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.23.2539