764650-92-2Relevant articles and documents
Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis
Sheth, Vishal M.,Hong, Bor-Cherng,Lee, Gene-Hsiang
, p. 3408 - 3412 (2017)
A concise and enantioselective synthesis of the tetracyclic indoles, including the naturally occurring compounds (+)-arborescidine C and (+)-arborescidine B, was achieved by the key step of Pictet-Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst. The synthetic process was further demonstrated in a pot-economy strategy and was achieved in a one-pot operation.
Regio-and enantioselective catalytic cyclization of pyrroles onto N-acyliminium lons
Raheem, Izzat T.,Thiara, Parvinder S.,Jacobsen, Eric N.
supporting information; experimental part, p. 1577 - 1580 (2009/04/07)
The regio- and enantioselective cyclization of pyrroles onto N-acyliminium ions generated in situ from hydroxylactams is reported. Modest to excellent ee's and yields are obtained in these novel Pictet-Spengler-type reactions with a chiral thiourea-pyrrole catalyst. Useful synthetic transformations of the versatile pyrroloindolizidinone and pyrroloquinolizidinone products are presented.
Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding
Raheem, Izzat T.,Thiara, Parvinder S.,Peterson, Emily A.,Jacobsen, Eric N.
, p. 13404 - 13405 (2008/09/16)
Highly enantioenriched indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiti
