ChemInform Abstract: Enantio‐ and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis‐Decahydroquinolines.

Identification of tetracyclic lactams as NMDA receptor antagonists with potential application in neurological disorders

“…human immunodeficiency virus protease inhibitors, aggrecanase inhibitors and malarial Plasmepsin inhibitors). [30][31][32] However, this scaffold was never used for the design of CNS agents. The target compounds were designed considering different substituents on the phenyl ring at position C-3a and the insertion of a small group on the lactam ring (position C-3).…”

Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline

“…As a consequence of their widespread distribution and different biogenetic origins, DHQ-containing alkaloids are structurally diverse in their substitution pattern and stereochemistry, which has stimulated the development of general methodologies and unified synthetic strategies for the stereoselective synthesis of substituted DHQ derivatives. 4 In this context, in previous work, we have used tricyclic aminoalcohol-derived oxazoloquinolone lactams as multipurpose enantiopure scaffolds for diastereoselective transformations into a variety of diversely substituted cisdecahydroquinolines, including the DHQ alkaloids (−)-pumiliotoxin C, 5 (−)-lepadins A-C, 6 (+)-lepadin D, 6b (+)-myrioxacin A, 7 and (+)-gephyrotoxin 287C 8 (Scheme 1). From the stereochemical standpoint, crucial steps in our syntheses of pumiliotoxin C and lepadins were a stereoselective cyclocondensation reaction of (R)-phenylglycinol with a cyclohexenone-derived δ-keto ester and the subsequent stereoselective hydrogenation of the resulting rigid cis-fused tricyclic lactams 1 6,9 (Scheme 2).…”

Total Synthesis of (−)-Cylindricine H

“…In recent work we have explored the stereoselective generation of chiral aminoalcohol-derived oxazoloquinolone tricyclic lactams and their transformation into diversely substituted cis-decahydroquinolines (DHQs). The relevance of these enantiomeric scaffolds in the total synthesis of alkaloids having in common a DHQ nucleus was illustrated with the total synthesis of Myrioneuron, 4 Lycopodium, 5 amphibian, 6 and marine alkaloids. 7 To further demonstrate the synthetic utility of these chiral tricyclic lactams, we decided to undertake the more challenging total synthesis of cylindricine H, which requires the formation of a quaternary carbon center embedded within a complex azatricyclic system.…”