No abstract

The constituents of the heartwood of Cedrela odorata are variable. The structure of methyl angolensate, one of the components, is elucidated on the basis of spectroscopic evidence and chemical transformations. It is a secoring-I3 tetranortriterpenoid closely related biogenetically to gedunin and deacetyl-7-keto-gedunin, which are also found in the heartwood.

Three triterpenes have been isolated from Cedrela odorata L. These are shown by chemical and spectroscopic evidence to be derivatives of tirucallol in which the side chain has been modified to a dihydroxytetrahydrofuran. , , 3312 cm.-l (OH) (Found: C, 75.9; H, 10-4; 0, 13.7. C30H5004 requires C, 75.9; H, 10.6; 0, 13.5%). Acetylation of the Cedrela Triterpenes.-This was done, in the standard way, with acetic anhydride and pyridine overnight a t room temperature. The products were isolated by dilution with water and filtration. Odoratol triacetate (V) was amorphous, v , , 1754 (OAc) cm.-l, 6 5.27 (lH, m, H-7), 5.12 (lH, q, J6.5 and 5.5 c./sec., H-23), 4-85 (lH, d, J 6.5 c./sec., H-24), 4-69 (lH, m, W J 5 c./sec., H-3), 4.02 (lH, d, J 5.5 c./sec., H-22), and 2.07 and 2.09 (6H and 3H respectively, each s, 3 x OAc) . Odoratone diacetate (11; R2 = Ac) gave needles, m.p. 222-224" (from methanol), vmx. 1754 (OAc) and 1710 (cyclohexanone) cm.-l, 6 5.34 ( l H , m, H-7), 5.13 ( l H , q, J 6-5 and 6.0 c./sec., H-23), 4.87 (lH, d, J -6.5 c./sec., H-24), 4.03 (lH, d, J 6.0 c./sec., H-22), and 2.08 and 2.11 (each 3H, s, 2 x OAc)

EXTRACTION of the West Indian cedar (Cedrela odorata L., Meliaceae) has given variable results.lp2The extract from one specimen has given in small amount, odoratin, ClBH22O4, m.p. 216-223", [a],+ 155' (CHCl,), for which we suggest structure (I).