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Extra resources for Alkaloids (v. 9)

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J. Zeiler, Tetrahedron, 1978, 34, 1979. The Alkaloids 38 aldehyde was converted into its diethyl acetal, which with ethyl vinyl ether and a Lewis acid gave the triethoxypropane (16);this, on heating with phosphoric acid, yielded the phenylacrylaldehyde (17). ' OEt (17) The chiroptical properties of pelletierine and anaferine have been studied. They reveal that both molecules are sensitive to conformational changes. The former apparently adopts the trans -pseudo-ring conformation (18) in acid solution and the cis-fused counterpart (19) in neutral solution.

B. Herbert in ref. 8, p. 27. 86*88 Earlier intermediates are known9*s37s4 to be secologanin (103) and tryptamine (102). Chemical condensation of these compounds affordsvincoside (109) and strictosidine (isovincoside) (104),which are epimeric at C-3. ^^ This has been puzzling because the first terpenoid indole bases to be formed have the 3a configuration. The recent publications have been concerned with the solution of this puzzle. This ~ ~ . ~material ~ was 87 *' *9 90 '* A. I. -L. Lee, J. Amer.

Furthermore, although ( 5 ) was not isolated from members of the Solanaceae, its isomer, - nor-(4), has been found in low yield in Brugmansia sanguinea6 0 OH (6) (4) Catuabines A, B, and C [(7), (8), and (9)] are new diester alkaloids’ from Erythroxylon vaccinifolium Martius. The surprising feature of (8) is that 3,4,5trimethoxybenzoic acid rather than pyrrole-2-carboxylic acid is the esterifying Me 0 OTMB 0 OTMB Me 0 \I O N H TMB = 3,4,5-trimethoxybenzoyl acid. r. r. spectra ascertained the P-configuration of the esterified hydroxyl function at C-6 (or -7).

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