355393-46-3Relevant academic research and scientific papers
An efficient construction of bridged chiral tetracyclic indolidines, a core structure of asperparaline, via stereocontrolled catalytic Pauson-Khand reaction
Tanimori, Shinji,Sunami, Tatsuya,Fukubayashi, Kouji,Kirihata, Mitsunori
, p. 2481 - 2492 (2005)
A reaction of chiral enyne 22 derived from l-proline with a catalytic amount of cobalt (0) octacarbonyl in the presence of N-methylmorphorine N-oxide gave tricyclic enone 24 in 54% yield (73% based on consumed starting material). Treatment of enone 11 with aqueous methylamine followed by silica gel afforded bridged tetracyclic indolidine 1, a common structural motif of natural metabolites, an asperparaline series of compounds and also a potential intermediate for the synthesis of a paralytic alkaloid, asperparaline C (4), in 70% yield.
A new pathway to chiral tetracyclic indolidines via Pauson-Khand reaction
Tanimori, Shinji,Fukubayashi, Kouji,Kirihata, Mitsunori
, p. 4013 - 4016 (2007/10/03)
Reaction of enynes 1 and 3 with Co2(CO)8 in the presence of DMSO, NMO or TMANO as promoters produced tricyclic indolidine derivatives 5 and 7 stereoselectively in moderate to excellent yield. The stereochemistry at the C-7 position of the indolidines 5 and 7 was confirmed by their conversion into the bridged azacycles 10 and 13.
