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Asymmetric Total Syntheses of (-)-Antofine and (-)-Cryptopleurine Using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol

Asymmetric Total Syntheses of (-)-Antofine and (-)-Cryptopleurine Using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol

Sanghee Kim, Taeho Lee, Eunjung Lee, Jaekwang Lee, Gao-jun Fan, Sang Kook Lee, Deukjoon Kim

J Org Chem. 2004 Apr 30;69(9):3144-9.

PMID: 15104454

Abstract:

The asymmetric total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, (-)-antofine and (-)-cryptopleurine, are described. An efficient synthetic pathway to the key intermediate 12, in enantiomerically pure form, was achieved by using a chiral building block (R)-9 and the Overman rearrangement with a total transfer of chirality. The problem of constructing the pyrrolidine and piperidine rings was successfully addressed, primarily by using a ring-closing metathesis reaction and a cross-metathesis reaction, respectively.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1105511656	2-(Tributylstannyl)-3-methoxypyrazine		1105511-65-6	Price

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