✦ LIBER ✦
Selective bis-hydride reduction of tosylmethyl-substituted tricyclic enones by lithium aluminium hydride synthesis of α-methylene cyclopentenoids
✍ Scribed by Adrie A.M. Houwen-Claassen; A.J.H. Klunder; B. Zwanenburg
- Book ID
- 104204648
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 839 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
On treatment with L.&l the I-tosylmethyl substituted exe-IO-oxan-icyclo[S~.l.~b]&c~e~~s 1 and 3 undergo two consecutive, regioselecrive and stereospecific reductions. The first reduction constitutes an S$' displacement of the allylic rosy1 group, the second a 1,2-reduction of the resulting exo-cyclic erwne to form the a-methylene cyclenols 7 and 8, respectively. These products are smoothly converted into a-methylenecyclopentenols and a-methylene-cyclopentenones, using the Flash Vacuum Thermolysis techmique for the required cycloreversion.
A. A. M. HOUWEN-CLAASSEN et al.