An efficient photochemical approach to the trans-bicyclo[5.1.0]octene ring system
β Scribed by Wood, John L.; Liverton, Nigel J.; Visnick, Melean; Smith, Amos B.
- Book ID
- 127355443
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 381 KB
- Volume
- 111
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
An efficient strategy for the rapid construction of the guiane bicyclo[5.3.0]decane ring system from appropriately substituted 4-alkyn-1-ols has been developed. This methodology relies on a MeLi-catalyzed tandem 5-exo-dig cyclization/Claisen rearrangement sequence as the key ring forming step.
A simple two step sequence for ihe construction of highly functionalised bicyclo[ 5.2.l]decane and its transformation to bicyclo[ 5.3.1]undecane is described for entry into bridged ring terpenoids.
An enantioselective method to prepare trans-fused bicyclo[5.3.0]decane systems is described. This methodology is based on two key reactions: a [4Ο©3] cycloaddition reaction (to generate the seven-membered ring) and the Nicholas reaction (to insert the five-membered ring). The application of this meth