A total synthesis of myrrhine, (±)-hippodamine, and (±)-convergine
- 1 February 1976
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 54 (3) , 473-481
- https://doi.org/10.1139/v76-064
Abstract
A seven-step, stereoselective, total synthesis of the ladybug defensive substance myrrhine (5) from 2,4,6-collidine is presented. Successive alkylation and acylation of 2,4,6-collidine followed by ketalization provides 2-(3-[2-(1,3-dioxolanyl)]propyl)-6-(2-methyl-2-[1,3-dioxolanyl]methyl)-4-methylpyridine (14). Sodium–alcohol reduction gives the corresponding all-cis piperidine 17. Hydrolysis of 17 followed by acid-catalyzed cyclization provides ketone 26. Reduction of the carbonyl group in 26 gives myrrhine (5). Cyclization using pyrrolidine – acetic acid gives a mixture of ketones (26 and 31). Reduction of 31 gives (±)-hippodamine (4). Oxidation of (±)-hippodamine with peracid gives (±)-convergine (3).This publication has 1 reference indexed in Scilit:
- The alkaloids of Lycopodium cernuum L. III. The synthesis of dihydrodeoxyepiallocernuineCanadian Journal of Chemistry, 1967