ISSN:
1434-4475
Keywords:
Chatancin
;
Stereoselective Synthesis
;
Enantiomerically pure highly substituted decalinones, acidic fragmentation
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary Our first target on the way towards the synthesis of enantiomerically pure chatancin is the preparation of the title compound. The cycloadduct of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and thymoquinone is stereo- and regioselectively reduced to the tricyclic ketoalcohol4, which by nucleophilic cyclisation and reductive removal of the keto group as well as the chlorine atoms yielded a tetracyclic dimethoxyketal. Acidic hydrolysis freed the keto group, which now was treated with a chiral lithium alkyl compound derived from methyl (R)-2-methyl-3-hydroxypropionate in few steps. The resulting stereomeric tertiary alkohols were fragmented and the decalinones thus obtained separated. X-ray analysis permitted the determination of the absolute configuration of these decalinone derivatives.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00812715
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