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Communication | Regular issue | Vol 9, No. 9, 1978, pp.1263-1269
Published online, 1st January, 1970
DOI: 10.3987/R-1978-09-1263
An Approach to the Skeleton of Rauwolfia Alkaloids. A General Synthesis of 3,8-Epoxy-7-keto-6-oxabicyclo[3.2.1]octane Derivatives

Toshio Suzuki, Akiko Tomino, Seiko Kagaya, Katsuo Unno, and Tetsuji Kametani*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Hydrolysis of the Diels-Alder adducts (1) and (2), followed by halolactonization, gave 4-bromo- (6) and 4-iodo-3-methoxycarbonyloxymethyl-3,8-epoxy-7-keto-6-oxabicyclo[3.2.1]octane-2-carboxylic acid (8), respectively. Arndt-Eistert reaction of the acid chloride (14), derived from 6, provided the methyl ester (16). The intermediate diazoketone (15) was also transformed to the amides (17) and (18) by condensation with tryptamine and 6-methoxytryptamine, respectively, both of which would be key intermediates for the synthesis of Rauwolfia alkaloids, deserpidine (12) and reserpine (13).