ISSN:
0170-2041
Keywords:
Michael addition, stereoselectivity
;
Indoloquinolizidones, enantiomerically pure
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Acylation of the carboline derivatives 6 and 9 with diketene affords the corresponding N-(acetoacetyl)carbolines 7 and 10, respectively. While 10 can be converted into a 1:2.1 mixture of the title compounds 11 a and 11 b on treatment with oxalic acid, the cyclic acetal 7 can only be cyclized to yield the pyridone derivative 8. Michael addition of methyl malonate to the unsaturated ketone 11 b proceeds with excellent stereoselectivity to generate the keto diester 12 a which, on treatment with a base is transformed into its diastereoisomer 12 b. In contrast to 11 b, its stereoisomer 11 a does not react with methyl malonate.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900160
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