Further reactions of sideridiol [(–)-kaur-15-ene-7β,19-diol]

Autor:	Franco Piozzi, Maria Luisa Marino, Aurora Bellino, P. Salvadori, Pietro Venturella
Rok vydání:	1972
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Base (chemistry) chemistry Diol Halogenation Organic chemistry Lactone Ene reaction
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :759-762
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19720000759
Popis:	The secondary hydroxy-group of sideridiol [(–)-kaur-15-ene-7β,19-diol](I) has been confirmed as being in the 7- rather than the 12-position. Bromination of methyl (–)-7-oxokauran-19-oate (IXb) gives methyl (–)-6β-bromo-7-oxokauran-19-oate (Xb); treatment of the latter with base gives (–)-7-oxokaur-5-en-19,6-olide (XII) mainly. Better yields of lactone (XII) are obtained by heating a solution of bromo-ester (Xb) in dimethyl sulphoxide under reflux. The n.m.r., o.r.d., and c.d. data for the bromo-ester (Xb) are discussed.
Databáze:	OpenAIRE
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