Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 26, No. 3, 1987, pp.721-730
Published online, 1st January, 1970
DOI: 10.3987/R-1987-03-0721
The Synthesis of the Isoquinoline Alkaloid Calycotomine via Functionalization of Enamide Double Bonds

George R. Lenz

*Department of Chemistry, G. D. Searle & Company, 4901 Searle ParkwaySkokie, Illinois 60077, U.S.A.


The novel alkaloid calycotanine, a 1-hydroxymethylenetetrahydroisoquinoline, has been synthesized from 1-methyl-3,4-dihydroisoquinoline via the 2-benzyloxycarbonyl enamide derivative. Oxidation of the enamide with osmim tetroxide results in bis-hydroxylation and ring opening to form hydroxyacetcphenone carbamates. Hydrogenation results in reclosure of the isoquinoline ring and further reduction yielding l-hydroxymethylenetetrahydroisoquinolines.