Structure of (±)-murrafoline, a novel biscarbazole alkaloid from Murraya euchrestifolia
✍ Scribed by Andrew T. McPhail; Tian-Shung Wu; Tomoko Ohta; Hiroshi Furukawa
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 158 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The structure and relative stereochemistry of (f)-murrafoline, a novel biscarbazole alkaloid isolated from Murraya euchrestifolia, have been established by spectral and singlecrystal X-ray analysis. Investigations of the root bark extracts from Murraya euchrestifoZia Hayata (Rutaceae), collected in Taiwan, have been reported elsewhere' to lead to the isolation of carbazole alkaloids in addition to new monomeric carbazole and carbazolequinone We here disclose the structure of the first example of a biscarbazole alkaloid, foline ($1, obtained from this source. novel bisalkaloids. (f)-murra-(?)-Murrafoline (t), C41H42N202, [m/z 594.3218 (M+, found); 594.3243, talc.] crystallized from MeOH-CH2C12 in the form of colorless needles {m.p. 260-262 'C (sint. 170 "Cl; In], 25 fO" (c 1.0, CHC13); vmax(CHC13): 3450, 1625, and 1610 cm-'] and gave U.V. spectral data typical of a carbazole nucleus2 [Amax (MeOH) (log E) 218(4.66), 243(4.86), 260(sh, 4.66), 307(4.45), and 332(sh, 3.91) nm]. The lH-n.m.r. (CDC13) spectrum contained signals attributable to two aryl IS 2.28, 2.37 (each 3H, s)], one vinyl [S 1.54 (3H, s)], and three oxygen-linked tertiary methyl groups [6 1.40 (3H, s), 1.44 (6H, s)] as well as a triplet [6 4.58 (lH, J = 8 Hz)], a multiplet 16 3.24 (lH)], and unresolved overlapping signals in the 6 6.
📜 SIMILAR VOLUMES
The structure and stereochemistry of murrangatid, a new monomeric coumarin isolated from the leaves of Murraya elongata Alph. DC (Rutaceae) has been reported by us recently. We now present the chemical and spectral evidence leading to the structure and stereochemistry of another new coumarin, murral