The synthesis of the title compound (VI), a brasilane sesquiterpenoid alcohol, is achieved from the (R)-pulegone derivative (I) in only three steps. The key to success is the diastereoselective radical addition of the tertiary radical derived from (II) to the electrophilic radicophile (I). -(COSSY,
โฆ LIBER โฆ
A very short and efficient synthesis of (+)-conocephalenol
โ Scribed by Janine Cossy; Samir BouzBouz; Abdelhak Hakiki
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 107 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The synthesis of (+)-conoeephalenol, a brasilane sesquiterpenoid alcohol, was achieved in seven steps from (R)-pulegone with an overall yield of 15%. The key steps were a radical addition of a tertiary radical to the eleetrophilic radicophile, (R)-3-methyl-2-methyleneeyclopentanone, and an aldol eyclization under acidic conditions.
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