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Towards a synthesis of (±)modhephene via cascade rearrangement: Synthesis and rearrangement of dispiro[3.0.4.2]undecanes to [3.3.3]propellanes

✍ Scribed by Lutz Fitjer; Marita Majewski; Andreas Kanschik


Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
147 KB
Volume
29
Category
Article
ISSN
0040-4039

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## Abstract Formation of (−)‐[4.3.3]propellane 4 from (−)‐14‐hydroxymodhephene (2) proceeds through a Wagner‐Meerwein rearrangement via C3C4 bond‐shift to give a stable intermediate, dimethylcyclohexadienyl cation A, which undergoes deprotonation. Herein, this mechanism was investigated by using a