Alkaloids, Garrya

The lactam (Formula 470) has been converted to Formula 471 which proved to be the enantiomer of a degradation product of atisine (209). This clarifies the stereochemistry of the atisine alkaloids, the garrya alkaloids, and related diterpenes (209). 

IV. Correlations and Absolute Stereochemistry of Atisine and Garrya Alkaloids.. 155... 

V. The Ternary Iminium Salts of the Atisine and Garrya Alkaloids. 166... 

With the absolute configuration of the atisine and Garrya alkaloids established, it is interesting to note that these compounds join the ranks of terpenes with antipodal stereochemistry of the A/B ring fusion as compared with that of the steroids, e.g., andrographolide, atisirene, cafestol. 

Still a third synthesis of the Garrya alkaloids has been reported by Valenta, Wiesner, and Wong 105, 106). This synthesis starts with... 

CCCXXVIa to the amine CCCXVIIIa which has already been converted to the Garrya alkaloids. 

Wiesner K, Figdor S K, Bartlett M F, Henderson D R 1952 Garrya alkaloids. I. The structure of garryine and veatchine. Can J Chem 30 608-626... 

Wiesner, K., and Z. Valenta Recent Progress in the Chemistry of the Aconite-Garrya Alkaloids. In Progress in the Chemistry of Organic Natural Products, Vol. 26, pp. 26-89. Wien Springer. 1958. 

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