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The conversion of 2-formyl-3-keto-9-methyl-Δ1,4-hexahydronaphthalene into a perhydroazulene derivative

✍ Scribed by Drury Caine; John F. DeBardeleben Jr.; School of Chemistry

Publisher
Elsevier Science
Year
1965
Tongue
French
Weight
247 KB
Volume
6
Category
Article
ISSN
0040-4039

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✦ Synopsis

We have found that on irradiation in aqueous acetic acid followed by base catalyzed defomylatlon of the c-de photo-product, the 2-fonqyl dienone III is converted into the5/7-fused dienone IV in 7% overall yield.

Ccmpound III was prepared from the octalone I (1) by a procedure similar to that employed by Edwards et al. (2) for the.preperation of 2--fowl-A 194 -3-keto steroids. Condensation of I with ethyl formate in the presence of sodium methoxide end reaction of the l@roxymetbylene derivative II [b.p. 116-11.8 (0.5mm.); 75% yield; x2' 250 (~10,500) and 306 mp (~5,600); e + NaoH 240 (411,700) and 360 mp (&;ooo); s.

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