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Acid‐Catalyzed Rearrangements for a Diastereoselective Entry into a New Fused Hexacyclic Heterocycle: (5 RS ,7a RS ,12 RS ,14a RS ,)‐4,5,7a,11,12,14,14a‐octahydro‐5,12‐dimethyl‐diindolo [1,7‐ bc : 1′,7′‐ gh ][2,6] naphthyridine
Author(s) -
Papageorgiou Christos,
Borer Xaver
Publication year - 1988
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.19880710521
Subject(s) - chemistry , pyrrolidine , oxindole , ring (chemistry) , yield (engineering) , catalysis , claisen rearrangement , stereochemistry , pyrolytic carbon , alcohol , medicinal chemistry , organic chemistry , pyrolysis , materials science , metallurgy
The title compound 1 was obtained in 10.3% overall yield via two acid‐catalyzed rearrangements and pyrrolidine formation. Thus, bi‐oxindole 6 afforded exclusively the thermodynamically stable cis ‐diazachrysene 7 which, after allylation, followed by aza‐ Claisen rearrangement gave alcohol 2 . Pyrolytic ring closure of the latter yielded 1 in highly diastereoselective fashion.