Synthetic study of bicyclo[5.2.1]dec-8-en-4-ones based on tandem anionic [1,3] and oxy-Cope rearrangements of 2-vinylbicyclo[3.2.1]oct-6-en-2-ols
β Scribed by Hiroki Hashimoto; Toshihiro Jin; Michinori Karikomi; Katsura Seki; Kazuo Haga; Tadao Uyehara
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 76 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a βFull Textβ option. The original article is trackable v
The synthesis of unique diquinanes, possessing four continuous methyl groups on the convex of the diquinane skeleton, has been achieved by employing a combination of pinacol-type rearrangement and efficient anionic [1,3] rearrangement strategies.
The anionic [1,3] rearrangement of both stereoisomenc bicyclo[3.2.1]oct-6-en-2-ols by treatment with KN(TMS)2 in toluene or in diglyme took place as a stereoconvergent route giving each of the stereoisomeric hydroxydiquinanes.
irradiation of 8-oxabicyclo[3.2.l]oct-6-en-2-ones results in a 1 ,Sacyl rearrangement. The initial photoproduct undergoes a subsequent reaction involving hydrogen transfer followed by intramolecular cycloaddition of a ketene intermediate.
## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a βFull Textβ option. The original article is trackable v