Synthesis of (+)-madindoline A and (+)-madindoline B.
The allene ether version of the Nazarov cyclization was used to construct the cyclopentane dione portion of madindolines A and B. The racemic cyclopentane dione from the Nazarov cyclization was converted to an enol ether that was combined with the chiral, nonracemic hydroxyfuroindoline in a Mannich reaction. Deprotection and oxidation led to (+)-madindoline A and (+)-madindoline B. [reaction: see text].
Wan
Lifeng
L
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.
Tius
Marcus A
MA
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003460:Crystallization; D003500:Cyclization; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007211:Indoles; C103158:madindoline A