A convergent synthesis of the cardenolide skeleton: Intramolecular aldol condensation via reduction of α-bromoketones

Journal of Organic Chemistry

Volumn 67, Issue 16, 2002, Pages 5669-5672

  Chapdelaine, Daniel ^a   Belzile, Julie ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC INTERMEDIATES;

ADDITION REACTIONS; CONDENSATION; ESTERS; REDUCTION;

SYNTHESIS (CHEMICAL);

2 CYCLOHEXENONE; ALPHA BROMOKETONE; BROMINE DERIVATIVE; CARDENOLIDE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; POLYMERIZATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

CARDENOLIDES; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037047556     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025612b     Document Type: Article

References (31)

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3. The aldol condensation is the result of a preferred attack of the double-Michael-issued enolate ion on the pro-S carbonyl of the cyclopentadione unit