Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing, Jiangsu 210093, China.
Chem Asian J. 2010 Jun 1;5(6):1382-8. doi: 10.1002/asia.201000073.
An efficient total synthesis of (S)-14-azacamptothecin has been accomplished in 10 steps and 56% overall yield from 5H-pyrano[4,3-d]pyrimidine 8. A mild Hendrickson reagent-triggered intramolecular cascade cyclization, a highly enantioselective dihydroxylation, and an efficient palladium-catalyzed transformation of an O-allyl into N-allyl group are the key steps in the synthesis. This work provides a much higher overall yield than the previous achievement and shows sound flexibility for the further applications that will lead to new bioactive analogues.
（S）-14-喜树碱的高效全合成已经完成，从 5H-吡喃并[4,3-d]嘧啶 8 经 10 步反应以 56%的总收率得到。温和的 Hendrickson 试剂引发的分子内级联环化、高对映选择性的二羟基化以及钯催化的 O-烯丙基到 N-烯丙基的转化是合成的关键步骤。这项工作的总收率比以前的成就高得多，为进一步应用提供了很好的灵活性，这将导致新的生物活性类似物的出现。
