Affiliation:
1. Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University
2. Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Molecules
Abstract
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.
Subject
Organic Chemistry,Catalysis
Cited by
2 articles.
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