31456-25-4Relevant articles and documents
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Sugasawa et al.
, p. 5109 (1972)
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Volkmann,R. et al.
, p. 5576 - 5577 (1971)
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A Concise Total Synthesis of (±)-Camptothecin
Chen, Fen-Er,Huang, Guan-Xin,Liu, Min-Jie,Liu, Qian
, p. E3 (2019)
A total synthesis of racemic camptothecin, characterized by a concise construction of the ring systems and easy functional group transformation, is described. A domino reaction consisting of a Heck reaction and an aza-intramolecular Michael addition to form the C ring serves as the first key step in the synthesis. The D ring was constructed by a simple Wittig-Horner reaction followed by removal of the protective groups. Hydroxymethylation, demethylation, and lactone formation reactions were performed in one-pot to construct the E ring under hydrobromic acid conditions. This work provides an efficient scheme for further synthetic exploration of camptothecin and its analogues.
Plant antitumor agents. IX. The total synthesis of dl-camptothecin.
Wani,Campbell,Brine,Kepler,Wall,Levine
, p. 3631 - 3632 (1972)
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A short synthesis of camptothecin.
Bradley,Buechi
, p. 699 - 700 (1976)
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Copper(I) iodide-promoted hydroxylation onto the lithium or potassium enolate of lactones and lactams
Nakazawa, Norio,Tagami, Keiko,Iimori, Hitoshi,Sano, Shigeki,Ishikawa, Tsutomu,Nagao, Yoshimitsu
, p. 2157 - 2170 (2001)
After enolization of lactones (1a,b) and lactams (2a,b) with lithium or potassium hexamethyldisilazide in THF, each resultant enolate was treated with a solution prepared by mixing copper(I) iodide, pyridine, and tert-butyl hydroperoxide or N-methylmorpho
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Danishefsky,S. et al.
, p. 2521 - 2524 (1973)
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Experiments on the synthesis of dl camptothecin. III. Total synthesis of dl camptothecin
Sugasawa,Toyoda,Sasakura
, p. 771 - 781 (1974)
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Synthesis of (±)-camptothecin using a [3+2] nitrone cycloaddition to construct the CDE ring moiety
Yu, Jurong,Depue, Jeffrey,Kronenthal, David
, p. 7247 - 7250 (2007/10/03)
A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye with tricylclic ketone affords camptothecin after further elaboration. Tricyclic ketone is prepared via a route employing a [3+2] nitrone cycloaddition and an intramolecular Knoevenagel condensation. A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye 2 with tricylclic ketone 3 affords camptothecin after further elaboration. Tricyclic ketone 3 is prepared via a route employing a [3+2] nitrone cycloaddition and an intramolecular Knoevenagel condensation.
