ISSN:
1434-4475
Keywords:
Stereoselective Synthesis
;
Fragmentation
;
Preparation and Photoreaction of an Endione
;
Photochemical Hydrogen Abstraction
;
Perhydronaphtho[1,8-bc]furan
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary The diketone3 was reduced to the diol which then was transformed to the tetracyclic diketal5 by treatment with sodium in ethanol. Protection of the remaining hydroxy group was followed by hydrolysis of the dimethylketal. The resulting ketone7 was stereoselectively converted to the tertiary alcohol by methyl magnesium chloride. Acidic retrograde aldol reaction of the tertiary alcohol led to the decalindione10, which was partially dehydrogenated by cupric chloride under basic conditions. The resulting endione1 cyclized by light induced hydrogen abstraction and collapse of the resulting diradical to the perhydronaphtho[1,8-bc]furan derivative.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01277639
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