Formal synthesis of (+/-)-dendrobine: use of the amidofuran cycloaddition/rearrangement sequence.
The formal synthesis of the alkaloid (+/-)-dendrobine (4) was accomplished using the IMDAF cycloaddition/rearrangement sequence of a furanyl carbamate. Conversion of the rearranged cycloadduct to Kende's advanced intermediate in eight steps completed the formal synthesis of (+/-)-dendrobine.
Padwa
A
A
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.chemap@emory.edu
Dimitroff
M
M
Liu
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B
D000470:Alkaloids / Q000138:chemical synthesis*; D002219:Carbamates / Q000737:chemistry; D000697:Central Nervous System Stimulants / Q000138:chemical synthesis*; D003292:Convulsants / Q000138:chemical synthesis*; D003500:Cyclization; D004365:Drugs, Chinese Herbal / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D002219:Carbamates; D000697:Central Nervous System Stimulants; D003292:Convulsants; D004365:Drugs, Chinese Herbal; D005663:Furans; C002077:dendrobine