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Enantioselective synthesis of indole alkaloids from chiral lactams
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This account reports on the use of (R)- or (S)-phenylglycinol- and (S)-tryptophanol-derived oxazolopiperidone lactams as building blocks for the enantioselective synthesis of structurally diverse indole alkaloids. 1 Introduction 2 Monoterpenoid Indole Alkaloids from (R)- or (S)-Phenylglycinol-Derived Lactams 2.1 Substituted Piperidines as Precursors for the Enantioselective Synthesis of Indole Alkaloids 2.1.1 (+)-Decarbomethoxytetrahydrosecodine 2.1.2 Enantiopure cis- and trans-(3-Ethylpiperidin-4-yl)acetates as Precursors for the Synthesis of Indolo- and Benzo-[a]quinolizidine Alkaloids 2.1.3 Indole Alkaloids Related to Cleavamine and Quebrach-amine 2.2 Uleine and Strychnos Alkaloids 2.3 The Ervatamine-Silicine Group 3 Indolo[2,3-a]quinolizidines from (S)-Tryptophanol-Derived Lactams 3.1 Indolo[2,3-a]quinolizidines and Analogues by Intramolecular Amidoalkylation Reactions: Synthesis of (R)-(+)-Deplancheine and (R)-(+)-Harmicine 3.2 Indolo[2,3-a]quinolizidines by a Modified Bischler-Napieralski Reaction: Formal Synthesis of (+)-Dihydrocorynantheine and (-)-Dihydrocorynantheol 4 Conclusion
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AMAT TUSÓN, Mercedes, PÉREZ BOSCH, Maria and BOSCH CARTES, Joan. Enantioselective synthesis of indole alkaloids from chiral lactams. Synlett. 2011. Vol. 2011, num. 2, pags. 143-160. ISSN 0936-5214. [consulted: 30 of May of 2026]. Available at: https://hdl.handle.net/2445/164346