Ochotensine and related compounds. II.   A synthesis of iso‐ochotensine. (Studies on the syntheses of heterocyclic compounds. CCLXXV  ) | Zendy

Kametani T. | Zendy; Takano S. | Zendy; Hibino S. | Zendy; Terui T. | Zendy

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Ochotensine and related compounds. II. A synthesis of iso‐ochotensine. (Studies on the syntheses of heterocyclic compounds. CCLXXV )

Author(s) -

Kametani T.,

Takano S.,

Hibino S.,

Terui T.

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.5570060109

Subject(s) - chemistry , wittig reaction , lithium (medication) , sodium hydride , aluminum hydride , methylene , lithium hydride , alkylation , medicinal chemistry , lithium aluminium hydride , organic chemistry , stereochemistry , ionic bonding , ion , medicine , catalysis , endocrinology , methoxide

In order to examine the total syntheses of ochotensine (1) and ochotensimine (II), one of the isomers, iso‐ochotensine (III), was synthesized as a preliminary experiment. Namely, Wittig reaction of VI, followed by treatment with sodium bicarbonate solution, gave the expected compound, 7‐ethoxycarbonyl‐3‐ethoxycarbonyloxy‐2‐methoxy‐13‐methyIene‐10,11‐methyIene‐dioxyochotensinan (VII) which was reduced with lithium aluminum hydride to give III. This was also obtained by methylation of 3‐hydroxy‐2‐methoxy‐13‐methylene‐10,11‐methyIenedioxy‐ochotensinan (VIII).

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