Journal
ORGANIC LETTERS
Volume 3, Issue 16, Pages 2505-2508Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol010106e
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[GRAPHICS] The total synthesis of the tetracyclic alkaloids stemonamide (1) and isostemonamide (2) is presented. The key step is the reaction between a silyloxyfuran and an N-acyliminium ion. The second quaternary center is created by an intramolecular aldol spirocyclization. After 1,4-addition of an appropriate side chain, the methyl and double bond are installed by Mannich reaction. The seven-membered ring is closed by intramolecular nucleophilic displacement.
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