A General Strategy to Aspidosperma Alkaloids:  Efficient, Stereocontrolled Synthesis of Tabersonine

Hypervalent iodine compounds derived from o-nitroiodobenzene and related compounds: syntheses and structures

“…6,7 Literature search has shown that a number of such compounds were described, but structural investigation had not been made at all, and their characterizations in many cases were insufficient. A number of o-nitrodiphenyliodonium salts is known for years -iodide, 8,11 bromide, 9,11 chloride, 11 fluoride, 10 nitrate, 11 tetrafluoroborate 12 and hexachloroplatinate, 12,13 . They are characterized by melting points and, in one case, by 127 I NQR study.…”

A Review on Recent Developments in Syntheses of the Post-Secodine Indole Alkaloids. Part I: The Primary Alkaloid Types

“…Even in this case the Fischer indolisation/reduction afforded some isomeric indole (13%), in addition to the desired (+)-aspidospermidine (183, 51%), which is an alkaloid from Melodinus morsei 76 .…”

“…An enantioselective synthesis of (-)-aspidospermine (194) by Shishido et al 77 utilises also Fischer indolisation of 184, the synthesis of which is based on a diastereoselective ring-closing olefin metathesis as the key step, Scheme 30. A lengthy preparation of the allylic alcohol 195 set the stage for Sharpless epoxidation (92%), and the resulting oxirane 196 was converted to alcohol 197a (91%).…”

Hypervalent iodine reagents in the total synthesis of natural products

“…435 The electron deficient 2-nitrophenyl group was chemoselectively transferred in this mild and base-free arylation.…”