First stekeospecific synthesis of E-γ-bisabolene. A method for the concurrent generation of a ring and a tetrasubstituted exocyclic double bond.
✍ Scribed by E.J. Corey; William L. Seibel
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 289 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A short stereospecific synthesis of E-y-bisabolene (A) from sn acyclic acetylenic precursor (either 2 or 9 is described. g+-bisabolene (I)l is a long known sesquiterpene which is broadly distributed in nature2 and of ccnsiderable biosynthetic interest as apredecessor of many cyclic and oxygenated terpenoids.
3 This relatively simple substance hitherto has not been synthesized in a stereocontrolled way for lack of a methodology which can generate specifically either an E or 2 exocyclfc tetrasubstituted olefin. 4 Indeed the stereocontrolled synthesis of exocyclic tetrasubstltuted olefins has remained as a classic unsolved general problem.