Synthetic Studies in the Indole Series. Preparation of the Unique Antibiotic Alkaloid Chuangxinmycin by a Nitro Group Displacement Reaction

Alan P. Kozikowski, Michael N. Greco, James P. Springer

Research output: Contribution to journalArticlepeer-review

Abstract

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 combines the nitro group displacement reaction with the Leimgruber indole synthesis to produce a 4-sulfur-substituted indole. Further transformations involving acetylation of the indole 3-position, an intramolecular Knoevenagel condensation to dehydrochuangxinmycin methyl ester, and a stereospecific hydrogenation reaction furnish chuangxinmycin methyl ester. The synthesis scheme does establish the cis relationship between the carboxylic acid and methyl group in the natural product.

Original languageEnglish (US)
Pages (from-to)7622-7626
Number of pages5
JournalJournal of the American Chemical Society
Volume104
Issue number26
DOIs
StatePublished - Jan 1 1982

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Synthetic Studies in the Indole Series. Preparation of the Unique Antibiotic Alkaloid Chuangxinmycin by a Nitro Group Displacement Reaction'. Together they form a unique fingerprint.

Cite this