Tetrahedron p. 11205 - 11212 (1993)
Update date:2022-08-03
Topics:
Takahata, Hiroki
Bandoh, Hiroshi
Momose, Takefumi
A short, practical and diastereoselective method for preparing the ant venom alkaloid, three (3R,5S,8aS)-3-alkyl-5-methylindolizidines (1-3), has been developed.The stereoselective intramolecular amidomercuration of the N-alkenylurethane 4 followed by oxidative demercuration provides the piperidine alcohol cis-6 as a major product.Thereafter, oxidation of cis-6 followed by the Horner-Emmons elongation of the ring appendages affords the enones 8, 10, and 11, which are stereoselectively converted into 1, 2, and 3, respectively, by catalytic hydrogenation.
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