Studies on the syntheses of heterocyclic compounds. Part 878. Synthesis of (±)-camptothecin and (±)-10-methoxycamptothecin via enamine annulation
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1563-1568
- https://doi.org/10.1039/p19810001563
Abstract
Synthesis of (±)-camptothecin (1) and (±)-10-methoxycamptothecin (2) was achieved via enamine annelation as a key step. Condensation of 3,4-dihydro-1-methyl-β-carbolines (9) and (10) with unsaturated tetra-esters (6) and (7) followed by reduction gave the indolo[a]quinolizin-4-ones (12) and (13). Photo-oxygenation of (12) and (13) and subsequent base treatment produced the indolizino[1,2-b]quinolones (16) and (17), which were converted into the pyridones (20) and (24). The former (20) had been correlated to (±)-camptothecin, while the latter (24) was transformed into (±)-10-methoxycamptothecin by application of the established method.This publication has 5 references indexed in Scilit:
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