The synthesis of tricyclo[4.3.0.03,8]Nonane (twist-brendane) and homoadamantane. A new route to homoadamantanes
β Scribed by B. Richard Vogt
- Publisher
- Elsevier Science
- Year
- 1968
- Tongue
- French
- Weight
- 209 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
In a recent communication (11, Schleyer and Aiskott pointed out that of the conceivable tricyclononanes only four (I-IV) do not possess three or four-membered rings or highly strained skeletons. Brendane (I), brexane (II) and noradamantane (III) are known (2). Be now wish to report the synthesis of the fourth member of this series, tricyclo[4.3.0.03'a1nonene (IV), colloquially termed "twist-brendane " (l), and to describe the unambiguous preparation of homoadamantsne (V) via a common intermediate.
III
π SIMILAR VOLUMES
An efficient strategy for the construction of and tricyclo[4.3.0.O4'lΒ°]decanes is described which involves a novel one-pot tandem acid-catalyzed rearrangement followed by an ene cyclization as key step and is exemplified by the total synthesis of pupukean-2-one 3.
Furthsr studies of ionizations of endo-bicyclo[2.l.O]pent-2-yl msnts on the nature of the various transition states involved: