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Highly stereocontrolled synthesis of [3.3.3] propellane sesquiterpenes. ( ± )-Modhephene and (±)-epimodhephene

✍ Scribed by Heinrich Schostarez; Leo A. Paquette


Book ID
103397730
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
602 KB
Volume
37
Category
Article
ISSN
0040-4020

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## Abstract The unusual propellane skeleton of the sesquiterpene modhephene (**1**) has been synthesized starting from cyclopentenone (**2**). The key step **6** → **7** is an efficient and highly stereoselective intramolecular thermal ene‐reaction. Further elaboration of the propellane **7** gave

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## Abstract The bis[6.3.3]propellane 6 derivative of 2,2′,6,6′‐tetramethylbiphenyl was, in the final stage, synthesized by dehydration, of octaalcohol 5. X‐ray structure analysis revealed the highly symmetric shape of the molecule and disordered oxygen atoms in the tetrahydrofuran rings. The dihedr