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Studies on the syntheses of heterocyclic compounds. part CCLXXIX . Synthesis of O ‐isobutylcularidine
Author(s) -
Kametani T.,
Iida H.,
Kibayashi C.
Publication year - 1969
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.5570060111
Subject(s) - chemistry , alkylation , lactone , stereochemistry , organic chemistry , catalysis
Although various methods of oxepine formation from phenoxybenzene dicarboxylic acids was attempted, only 11‐hydroxy‐4‐isobutoxy‐7,8‐dimethoxydibenz[ b,f ]oxepin‐l‐ylaeetic acid lactone (XXX) was synthesized successfully. Compound XXX gave O ‐isobutylcularidine (XXXVlIb) in a few steps. Our synthetic O ‐isobutylcularidine was identical with that prepared from natural cularidine proving the structure for cularidine proposed by Manske. However, dealkylation of synthetic O ‐isobutylcularidine was unsuccessful.