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Preparation of harringtonine from cephalotaxine

, : Preparation of harringtonine from cephalotaxine. Journal of Organic Chemistry 44(1): 63-67

Use of a racemic compound as a side-chain synthon provides a 3-step conversion of l-cephalotaxine into a readily separable, .apprx. 1:1 mixture of the clinically useful anticancer drug harringtonine and its side-chain epimer. The synthesis of the racemic compound is described.

Accession: 006173196

DOI: 10.1021/jo01315a015

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Related references

Hiranuma S.; Hudlicky T., 1982: Synthesis of homo harringtonine and its derivative by partial esterification of cephalotaxine. Tetrahedron Letters 23(34): 3431-3434

Wickremesinhe, E.R.M.; Arteca, R.N., 1996: HPLC separation of cephalotaxine, harringtonine and homoharringtonine from callus and root cultures of Cephalotaxus harringtonia. A simple extraction and analytical protocol was developed to assay cephalotaxine, harringtonine, and homoharringtonine from callus and root cultures of C. harringtonia. The process involves extraction by methanol followed by partitioning between 0...

Anonymous, 2007: Convergency and divergency as strategic elements in total synthesis: (+/-)-Cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine

Gitterman A.; Parry R.J.; Dufresne R.F.; Sternbach D.D.; Cabelli M.D., 1980: Biosynthesis of the cephalotaxus alkaloids biosynthesis of deoxy harringtonine iso harringtonine and harringtonine. Precursor incorporation experiments were used to investigate the biosynthesis of the antitumor Cephalotaxus alkaloids deoxyharringtonine (2), isoharringtonine (3) and harringtonine (4). It was established that the acyl portion of deoxyharringtonin...

Schwab J.M.; Parry R.J.; Foxman B.M., 1975: Cephalotaxine chemistry unusual addition reactions of seco cephalotaxine derivatives. Journal of the Chemical Society Chemical Communications (22): 906-907

L.Y.H.; Guo S F.; Zhou F Y.; X.S.Z.; Zhang H L., 1983: Combined harringtonine or homo harringtonine chemo therapy for acute nonlymphocytic leukemia in 25 children. Children (25) with acute nonlymphocytic leukemia (ANLL) were treated by combined chemotherapy, harringtonine or homoharringtonine, oncovin and prednisone (HOP) and HO from July 1977 to May 1980. Fifteen of 25 cases achieved complete remission (CR)...

Zhang, Z.Y.; Hou, C.H.; Zhu, Y.F.; You, X.Y.; Li, J.L.; Fu, Z., 1987: Curative effect of harringtonine semisynthetic harringtonine and HOAP on nonlymphocytic leukemias. Analysis of 304 cases. A study of treatment of 304 cases of nonlymphocytic leukemia with the ester alkaloid of harringtonine is reported. Among them, 216 patients were given the ester alkaloid of harringtonine or semisynthetic harringtonine alone. There were 93 acute my...

Liu, Q.; Ferreira, E.M.; Stoltz, B.M., 2007: Convergency and divergency as strategic elements in total synthesis: the total synthesis of (-)-drupacine and the formal total synthesis of (+/-)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine. [GRAPHICS]A concise route toward the syntheses of (-)-drupacine and (+)- and (-)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an imp...

Yongji Z.; Hui Yu; Xueying L.; Yongxing Z.; Wenjun L.; Xueli L.; Yuying Y., 1979: Experimental studies on the toxicity of harringtonine and homo harringtonine. Harringtonine (HA) and homoharringtonine (HO), 2 new antileukemic agents, are submitted to experimental toxicity studies in mice, rabbits and dogs. The organs involved in rabbits and dogs after 5 or 7 days' treatment with either alkaloid are...

Tang, L.J.; Weng, G.Y., 1985: Preparation and stability of liposome-associated harringtonine. Yao Xue Xue Bao 20(6): 463-469