Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento 35, 56126 Pisa, Italy.
Chirality. 2011 Oct;23(9):730-5. doi: 10.1002/chir.21008. Epub 2011 Aug 19.
Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biological activity. This article relates the results that we obtained in the field of the total synthesis of indolizidines from α-amino acids, based on the rhodium-catalyzed hydroformylation of N-allylpyrroles intermediates. The formed pyrrolylbutanals undergo an intramolecular cyclodehydration to 5,6-dihydroindolizines, which are fully hydrogenated to indolizidines. All reaction sequences are stereocontrolled: indeed, the chiral center in the starting amino acid is transferred into 5,6-dihydroindolizine moiety with complete stereochemical integrity and the new stereogenic center at C9 carbon atom in the final indolizidines is generated in only one configuration.
吲哚里西啶生物碱因其结构多样性和多样的生物活性而引起了广泛关注。本文介绍了我们在α-氨基酸全合成吲哚里西啶领域的研究成果，该成果基于铑催化的 N-烯丙基吡咯中间体的加氢甲酰化反应。形成的吡咯丁醛经历分子内环脱水反应生成 5,6-二氢吲哚嗪，然后将其完全氢化生成吲哚里西啶。所有反应序列均受立体控制：实际上，起始氨基酸中的手性中心被转移到 5,6-二氢吲哚嗪部分，具有完全的立体化学完整性，而最终吲哚里西啶中 C9 碳原子上的新立体中心仅以一种构型生成。
