Terpenoids-XXXII: absolute configuration of junenol and laevojunenol and synthesis of junenol from costunolide

Shaligram, A. M. ; Rao, A. S. ; Bhattacharyya, Sasanka Chandra (1962) Terpenoids-XXXII: absolute configuration of junenol and laevojunenol and synthesis of junenol from costunolide Tetrahedron, 18 (8). pp. 969-977. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)92751-6

Abstract

The north Indian vetiver variety has yielded a new laevo-rotatory crystalline sesquiterpene alcohol, which is named as laevojunenol. It is the optical antipode of the previously isolated dextrorotatory alcohol, junenol. The absolute configuration of these two alcohols, which belong to eudesman group of compounds has been determined on the basis of the synthesis of dihydrojunenol from santanolide 'c'. The dextrorotatory alcohol junenol has also been similarly synthesized from the new unsaturated lactone (XII), derived from the ten-membered carbocyclic lactone costunolide.

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