Enantioselective synthesis of indole alkaloids from chiral lactams

Abstract

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