A new route to the cis–anti–cis triquinane ring system. The synthesis of 4,4-dimethyltricyclo[6.3.0.02,6]undecan-3-one via β-enolate rearrangement
- 1 October 1984
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 62 (10) , 1926-1929
- https://doi.org/10.1139/v84-330
Abstract
A synthesis of cis, anti, cis-4,4-dimethyltricyclo[6.3.0.02.6]undecan-3-one is described in which the key step is .beta.-enolate rearrangement of 9.9-dimethyltricyclo[5.3.1.01.5]undecan-10-one proceeding with retention of configuration. The required [5.3.1.01.5] ketone was prepared in 6 steps from tricyclo[5.2.1.01.5]dec-8-ene. This sequence constitutes a new route to the tricyclo[6.3.0.02.6]undecane ring system characteristic of the hirsutane sesquiterpenes. The 13C data for several tricyclic derivatives was reported. [The use of this compound as an antitumor and antibiotic agent was outlined.].This publication has 2 references indexed in Scilit:
- Iterative three-carbon annelation. A stereoselective total synthesis of (.+-.)-hirsutic acid CJournal of the American Chemical Society, 1983
- Synthesis of coriolin. An approach to a functionalized BC ring systemThe Journal of Organic Chemistry, 1982