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Stereospecific synthesis of the (3aα,11α,12aα)‐decahydrobenzo[ a ]pyrrolo[3,2‐ g ]quinolizine ring system
Author(s) -
Clark Robin D.,
Nelson Janis T.,
Repke David B.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300338
Subject(s) - chemistry , stereospecificity , ring (chemistry) , stereochemistry , organic chemistry , catalysis
A stereospecific synthesis of racemic (3aα,11bα,12aβ)‐1,2,3,3a,4,6,7,11b,12,12a‐decahydro‐9‐methoxy‐1‐(methylsulfonyl)benzo[α]pyrrolo[3,2‐ g ]quinolizine (2) is reported. Cyclocondensation of lithiated pyrrolecarboxamide 5 and dihydroisoquinoline 6 afforded the key tetracyclic intermediate 7 . Hydrogenation of 7 gave the 3aα,11bα,12aα‐isomer 9 which was subsequently converted to 2 .
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