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A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)‐modhephene. Preliminary communication
Author(s) -
Oppolzer Wolfgang,
Marazza Fabrizio
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640537
Subject(s) - propellane , chemistry , stereoselectivity , sesquiterpene , intramolecular force , cyclopentenone , stereochemistry , enone , bicyclic molecule , organic chemistry , catalysis
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 the enone 10 which had been previously converted to (±)‐modhephene ( 1 ) in three steps.