Production of (-)dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b] furan
AssigneeQuest International B.V.
InventorsDerek H. R. Barton, Dennis K. Taylor, Chi-Lam Tse
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Abstract
Preparation of a methyl ketone intermediate useful in the synthesis of (-)-dodecahydro-3a,6,6, 9a-tetramethyl-naphtho(2,1-b) furan by subjecting (-)-sclareol to ozonolysis in the presence of iodine or iodine-containing compound. The intermediate can be converted to (-)-dodecahydro-3a,6,6,9a-tetramethyl-naphtho(2,1-b) furan by Baeyer-Villiger oxidation followed by reduction of the resulting product in the presence of a Lewis acid.
Claims12
In a process for preparing (-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b) furan of the formula (1):
- ##STR7## which comprises:
- (i) converting sclareol of the formula (2) ##STR8## to methyl ketones of the formulae:
- ##STR9## (ii) converting said ketone (4a) or mixture thereof with (4b) to, respectively, an acetate of the formula (5a) or mixture of acetates (5a) and (5b):
- ##STR10## and (iii) converting said acetate (5a) or acetate mixture (5a) and (5b) to said compound (1), the improvement which comprises carrying out step (i) by ozonolysis of the sclareol in the presence of iodine or an iodine-liberating compound.
A process for preparing a methyl ketone of formula 4(a) or 4(b) ##STR11## which comprises subjecting sclareol to ozonolysis in the presence of iodine or an iodine-containing compound.
Dependencies are inferred from the claim text.