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A novel method for the synthesis of diquinanes based on anionic [1,3] rearrangement of bicyclo[3.2.1]oct-6-en-2-ols
β Scribed by Hiroki Hashimoto; Yasuhiko Abe; Yasuyoshi Mayuzumi; Michinori Karikomi; Katsura Seki; Kazuo Haga; Tadao Uyehara
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 65 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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.
π SIMILAR VOLUMES
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.
Diquinane Synthesis Based on Anionic (1, 3) Sigmatropic Rearrangements of an Oxy-Cope System Incorporated in the Bicyclo(3.2.1)oct-6-ene Framework. -Treatment of 2-vinylbicyclooctenols (I) and (V) with KH in an appropriate solvent results in the formation of the (5-5) fused-ring compounds (II) and (
Stereoconvergent Approach to Each of the Stereoisomeric Hydroxydiquinanes Based on the Anionic [1,3] Rearrangement of Bicyclo[3.2.1]oct-6-en-2-ols. -The anionic [1,3] rearrangement of both stereoisomeric bicyclo-octenols (I) and (IV) by treatment with KN(Tms) 2 in toluene or diglyme takes place as