Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation.
[Structure: see text] A new and efficient synthetic route to chiral 3-substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L-tryptophan. The key step relies on the one-pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.
Song
Hao
H
Department of Chemistry of Medicinal Natural Products and Key Laboratory of Drug Targeting, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China.
Yang
Jun
J
Chen
Wei
W
Qin
Yong
Y
D003521:Cyclopropanes / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D007211:Indoles; D011758:Pyrroles; C030797:cyclopropane