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A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; Fabrizio Marazza

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
212 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 the enone 10 which had been previously converted to (±)‐modhephene (1) in three steps.

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## Abstract The synthesis of 3,3‐dialkyl‐3,4‐dihydroisoquinolines via heterocyclization in three‐component reaction of an activated arene with isobutyraldehyde and nitriles is described. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:486–493, 2004; Published online in Wiley InterScience (www.int