Studies on the syntheses of heterocyclic compounds. part CCLXXIX  . Synthesis of  O ‐isobutylcularidine | Zendy

Kametani T. | Zendy; Iida H. | Zendy; Kibayashi C. | Zendy

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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.

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