A 4+3 cycloaddition approach to the spatane ring system
β Scribed by Michael Harmata; Paitoon Rashatasakhon
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 61 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The adduct of dichloroketene and cyclopentene was converted to a tricyclo[5.3.0.0 2,6 ]decane ring system using a 4+3 cycloaddition reaction followed by a quasi-Favorskii rearrangement as the key steps.
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Heating azidcdienes 19 at 70Β°C produced the tricyclic 3-pyrrolines 20 and 21 in one operation. The diastereoselectivity of this process was examined, and found to be controlled by the conformation of the cyclization precursor. Compound 20d incorporates the basic features of gephyrotoxin 3. Fused bi
## Abstract magnified image Cycloadditions of __C,N__βdiarylnitrones to Ξ²βnitrostyrenes occurred to yield two diastereoisomeric cycloadducts, the 3,4β__trans__β4,5β__trans__ substituted isoxazolidine derivatives being formed selectively as the major products. These were characterised by spectrosco