Total Synthesis of the Duocarmycins

The total synthesis of (+)-duocarmycin A and SA through a common indoline intermediate is described. The key reactions include selective lithiation of a 2,6-dibromoiodobenzene derivative and diastereoselective addition to a chiral nitroalkene, copper-mediated aryl amination, and addition of aryllith...

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Veröffentlicht in:	Journal of the American Chemical Society 2003-06, Vol.125 (22), p.6630-6631
Hauptverfasser:	Yamada, Ken, Kurokawa, Toshiki, Tokuyama, Hidetoshi, Fukuyama, Tohru
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics, Antineoplastic - chemical synthesis Antineoplastic agents Biological and medical sciences Chemistry Exact sciences and technology General aspects Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Indoles Medical sciences Organic chemistry Pharmacology. Drug treatments Preparations and properties Pyrroles - chemical synthesis Pyrrolidinones - chemical synthesis Stereoisomerism Streptomyces - chemistry
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Beschreibung
Zusammenfassung:	The total synthesis of (+)-duocarmycin A and SA through a common indoline intermediate is described. The key reactions include selective lithiation of a 2,6-dibromoiodobenzene derivative and diastereoselective addition to a chiral nitroalkene, copper-mediated aryl amination, and addition of aryllithium to azlactones.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja035303i