86486-10-4Relevant academic research and scientific papers
Organocatalytic asymmetric mannich cyclization of hydroxylactams with acetals: Total syntheses of ( )-epilupinine, ( )-tashiromine, and ( )-trachelanthamidine
Koley, Dipankar,Krishna, Yarkali,Srinivas, Kyatham,Khan, Afsar Ali,Kant, Ruchir
supporting information, p. 13196 - 13200 (2015/02/19)
An asymmetric, organocatalytic, one-pot Mannich cyclization between a hydroxylactam and acetal is described to provide fused, bicyclic alkaloids bearing a bridgehead N atom. Both aliphatic and aromatic substrates were used in this transformation to furnish chiral pyrrolizidinone, indolizidinone, and quinolizidinone derivatives in up to 89% yield and 97% ee. The total syntheses of (-)-epilupinine, (-)-tashiromine, and (-)-trachelanthamidine also achieved to demonstrate the generality of the process.
Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis: Applications to Pyrrolizidine Alkaloids
Keck, Gary E.,Cressman, Erik N. K.,Enholm, Eric J.
, p. 4345 - 4349 (2007/10/02)
Syntheses of (+/-)-isoretronecanol, (+/-)-supinidine, (-)-dihydroxyheliotridane, and (+)-heliotridine are detailed.The key step in each case involves an intramolecular acyliminium ion cyclization onto a suitably positioned allylstannane for construction o
COMPLETELY REGIOSELECTIVE α-ACYLIMINIUM ION CYCLIZATIONS WITH ALLYL AND PROPARGYL SILANES
Hiemstra, Henk,Speckamp, W. Nico
, p. 1407 - 1410 (2007/10/02)
Intramolecular reactions of α-acyliminium ions with allyl and propargyl silanes occur under the influence of trifluoroacetic acid, to afford in high yield and with complete regioselectivity bridgehead nitrogen bicyclic compounds 5 - 8.
