Tetrahedron Letters p. 5683 - 5686 (1996)
Update date:2022-08-03
Topics:
Fortunak, Joseph M.D.
Kitteringham, John
Mastrocola, Antonietta R.
Mellinger, Mark
Sisti, Nicolas J.
Wood, Jeffery L.
Zhuang, Zhi-Ping
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.
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