阿米沙米类化合物的全合成。
Total synthesis of the ammosamides.
机构信息
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, California 92093-0204, USA.
出版信息
J Am Chem Soc. 2010 Mar 3;132(8):2528-9. doi: 10.1021/ja9106572.
Abstract
The ammosamides A-C are chlorinated pyrrolo[4,3,2-de]quinoline metabolites isolated from the marine-derived Streptomyces strain CNR-698. The natural products, which possess a dense array of heteroatoms, were synthesized in 17-19 steps from 4-chloroisatin. That the five nitrogen atoms were introduced at the appropriate time and in a suitable oxidation state was key to the success of the total synthesis. Compared to synthetic deschloro ammosamide B, natural ammosamide B is much less susceptible to oxidative degradation.
摘要
Ammosamides A-C 是从海洋来源的链霉菌菌株 CNR-698 中分离得到的氯化吡咯并[4,3,2-de]喹啉代谢物。这些天然产物含有大量的杂原子，由 4-氯邻氨基苯甲酸经过 17-19 步反应合成。在合适的时间以适当的氧化态引入五个氮原子是全合成成功的关键。与合成的去氯氨甲酰胺 B 相比，天然氨甲酰胺 B 更不易发生氧化降解。
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