Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 24, Pages 11101-11108Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302157e
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Funding
- Japan Society for the Promotion of Science
- Grants-in-Aid for Scientific Research [10F00422] Funding Source: KAKEN
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Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids (+)-dysoxyline (1), (+)-colchiethanamine (2), and (+)-colchiethine (3) are described. In the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline with aromatic aldehydes, performed by using the Julia-Kocienski reaction, afforded the corresponding 1(beta-styryl)-substituted tetrahydroisoquinolines with complete retention of the absolute configuration at the C1 carbon atom. Functionalization of the products generated in these processes by using four- or five-step sequences gave the target alkaloids 1-3.
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