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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).