83602-20-4Relevant academic research and scientific papers
Synthetic Studies in the Indole Series. Preparation of the Unique Antibiotic Alkaloid Chuangxinmycin by a Nitro Group Displacement Reaction
Kozikowski, Alan P.,Greco, Michael N.,Springer, James P.
, p. 7622 - 7626 (1982)
The total synthesis of the unique sulfur-containing antibiotic indole alkaloid chuangxinmycin is described.This compound, first isolated by Chinese chemists at the Institute of Materia Medica, was assembled from 2,6-dinitrotoluene by a scheme that combine
New, concise route to indoles bearing oxygen or sulfur substituent at the 4-position. Synthesis of (±)- and (S)-(-)-pindolol and (±)-chuangxinmycin
Ishibashi,Akamatsu,Iriyama,Hanaoka,Tabata,Ikeda
, p. 271 - 276 (2007/10/02)
A new method for the synthesis of 4-alkoxy- and 4-[alkyl (or aryl)thio]indoles has been developed by using the indolone 3 as a common intermediate. The indolone 3 was prepared from N-(phenylsulfonyl)pyrrole (7) and the α-chlorosulfide 8 in four steps. Heating of a mixture of 3 and an appropriate alcohol in the presence of p-toluenesulfonic acid and cupric chloride afforded the 4-alkoxyindoles 11a-d. The method was applied to the synthesis of (±)-pindolol (19) and (S)-(-)-pindolol (20). Thiols also reacted with 3 in the presence of boron trifluoride to give 4-[aryl (or alkyl)thio]indoles 12, 21a, b, and 22a-d. The (indol-4-ylthio)acetate 22c was employed as a key intermediate for a concise total synthesis of (±)- chuangxinmycin (27).
A new, general entry to 4-substituted indoles. Synthesis of (S)-(-)-pindolol and (±)-chuangxinmycin
Ishibashi, Hiroyuki,Tabata, Takashi,Hanaoka, Kyoko,Iriyama, Hiroko,Akamatsu, Susumu,Ikeda, Masazumi
, p. 489 - 492 (2007/10/02)
A new method for synthesis of 4-substituted indoles has been developed by using the 7-arylthio-6-7-dihydroindol-4(5H) one 5 as a common intermediate. The method was applied to the synthesis of (S)-(-)-pindolol (11) and (±)-chuangxinmycin (16).
