161681-84-1Relevant articles and documents
Novel syntheses of camptothecin alkaloids. Part 2. Concise synthesis of (S)-camptothecins
Fortunak, Joseph M.D.,Kitteringham, John,Mastrocola, Antonietta R.,Mellinger, Mark,Sisti, Nicolas J.,Wood, Jeffery L.,Zhuang, Zhi-Ping
, p. 5683 - 5686 (1996)
A 9-step, convergent total synthesis of (S)-camptothecin alkaloids is described. The intramolecular [4 + 2] cycloaddition of an N-arylimidate with an alkyne is used to prepare the alkaloid ABC ring system. The chiral center is derived utilizing Seebach's chemistry for the diastereoselective Michael addition of a chiral dioxolanone enolate to a methylene malonate acceptor. The total synthesis of non-racemic topotecan is accomplished from (S)-10-hydroxycamptothecin in an additional step.