Kutney, James P. ; Cable, John ; Gladstone, William A. F. ; Hanssen, Harald W. ; Vijay Nair, G. ; Torupka, Edward J. ; Warnock, William D. C. (1975) Synthetic studies in the Veratrum alkaloid series. II. The total synthesis of verarine, veratramine, jervine, and veratrobasine Canadian Journal of Chemistry, 53 (12). pp. 1796-1817. ISSN 0008-4042
Full text not available from this repository.
Official URL: http://www.nrcresearchpress.com/doi/abs/10.1139/v7...
Related URL: http://dx.doi.org/10.1139/v75-252
Abstract
Coupling of 3β-acetoxy-5α-etiojerv-12(13)-en-17-one (1) with the lithio derivative of 2-ethyl-5-methylpyridine provides the crucial intermediate (3) for the subsequent elaboration to verarine. Aromatization of 3 to 4 and reduction of the latter provides a mixture from which N-acetyl-5α,6-dihydroverarine (11) was isolated. Subsequent introduction of the 5,6-double bond in the latter and removal of the N-acetate function completed the synthesis of verarine (31). In a similar sequence of reactions employing 1 and the lithio derivative of 2-ethyl-3-methoxy-5-methyl-pyridine, the resultant intermediate (54), was elaborated to 5α,6-dihydroveratramine (56). Due to known conversions of the latter to veratramine (14), jervine (32), veratrobasine (33), and 11-deoxojervine (34), the formal total synthesis of these natural products is complete.
Item Type: | Article |
---|---|
Source: | Copyright of this article belongs to NRC Research Press. |
ID Code: | 58033 |
Deposited On: | 31 Aug 2011 12:41 |
Last Modified: | 31 Aug 2011 12:41 |
Repository Staff Only: item control page