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Synthesis of 2-azabicyclo[3.3.1]nonan-3,7-diones and their fischer indolization

✍ Scribed by Mercedes Amat; Enric Sanfeliu; Josep Bonjoch; Joan Bosch

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
252 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new, efficient synthetic route to functionalized morphans 6 based on the intramo- lecular amidoalkylation of enamides 5 and the first synthesis of 3-oxoderivatives of' the hexahydro-1,5-methanoazocino [4,3_b]indole system are reported.

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## Abstract The azabicyclic __endo__ compound 3 was synthesized by reaction of enamine 1 with 2‐benzoyl‐1,3‐dichloropropane (2). The thermodynamically more stable __exo__ isomer 4 was obtained by epimerization of 3 with sodium methoxide. The reduction of 3 and 4 was carried out with different reduc