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The synthesis of tricyclo[4.3.0.03,8]Nonane (twist-brendane) and homoadamantane. A new route to homoadamantanes

✍ 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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✦ 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


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A highly flexible route to tricyclo[4.3.
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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.