40899-84-1Relevant academic research and scientific papers
Halogen-magnesium exchange reaction of iodoindole derivatives
Kondo, Yoshinori,Yoshida, Akihiro,Sato, Shuichiroh,Sakamoto, Takao
, p. 105 - 108 (2007/10/02)
Halogen-magnesium exchange reaction of iodoindoles with ethylmagnesium bromide in THF undergoes smoothly to give indolylmagnesium bromides which react with various electrophiles.
Magnesiation of indoles with magnesium amide bases
Kondo, Yoshinori,Yoshida, Akihiro,Sakamoto, Takao
, p. 2331 - 2332 (2007/10/03)
1-Substituted indole derivatives are deprotonated with Hauser bases (R2NMgBr) or magnesium diamide [(R2N)2-Mg] to give magnesioindoles which are then reacted with electrophiles.
Preparation and reactions of lithium indolyl(dimethyl)zincates
Kondo, Yoshinori,Takazawa, Nobuo,Yoshida, Akihiro,Sakamoto, Takao
, p. 1207 - 1208 (2007/10/02)
Lithium indol-3-yl(dimethyl)zincates, prepared by halogen-zinc exchange of 3-iodo-1-phenylsulfonylindoles with lithium trimethylzincate, reacted with benzaldehyde to give the corresponding alcohols.
Preparation of alkyl-substituted indoles in the benzene portion. Part 9. Synthesis of (1aS,8bS)-1-tert-butyloxycarbonyl-8-formyl-1,1a,2,8b-tetrahydroazirino [2',3':3,4]pyrrolo[1,2-a]indole. Model study for the enantiospecific synthesis of ziridinomitosenes
Utsunomiya,Fuji,Sato,Natsume
, p. 854 - 860 (2007/10/02)
Effective pathways for an enantiospecific synthesis of (1aS,8bS)-1-tert-butyloxycarbonyl-8-formyl-1,1a,2,8b-tetrahydroazirino [2',3':3,4]pyrrolo[1,2-a]indole (8) were investigated as a preliminary experiment aiming at chiral syntheses of aziridinomitosenes 5 and (1aS,8bS)-8-[[(aminocarbonyl)oxy]methyl]-5-formyl-7-hydroxy-1,1a,2,8b- tetrahydroazirino[2',3':3,4]pyrrolo[1,2-a]indole (6a). An aldehyde 14, derived from L-serine was condensed with 2-lithio-1-(phenylsulfonyl)indole (10) to afford diastereomers 15a and 15b, whose stereochemistry was unambiguously determined by 1H-NMR studies of the 1,3-dioxane derivatives 17a, 17b, and 18 as well as the X-ray crystallographic analysis of a dihydropyrrolo[1,2-a]indole derivative 31a. The latter compound was prepared from 15a via the following operations (Chart 5): (i) removal of the acetonide and the indole-protecting groups, followed by acetylation to form 29a, (ii) Vilsmeier reaction to produce 30a, and (iii) hydrolysis of acetyl groups, partial methanesulfonylation (mesylation), and treatment with potassium carbonate in acetonitrile. A diastereomer 31b was obtained from 15b in a similar manner. Both isomers 31a and 31b afforded the desired compound 8 upon treatment with a mesylation reagent followed by potassium tert-butoxide in tetrahydrofuran.
