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A Novel Total Synthesis of Antibiotic Carbazole Alkaloid Carbazomycin G

✍ Scribed by Hitomi Hagiwara; Tominari Choshi; Hiroyuki Fujimoto; Eiichi Sugino; Satoshi Hibino

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
101 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐA total synthesis of carbazomycin G (1) has been newly completed in seven steps. The 1,3-dioxygenated carbazole (4) via the 3-methoxy-1-methoxymethyloxycarbazole (11) as a synthetic precursor was synthesized by using the allene-mediated electrocyclic reaction of a 6p electron system generating from the 2-propargylindole derivative (10), which was derived from the 3-vinylindole (8) in three steps. Finally, the oxidation of the phenol (4) followed by the addition of methyl lithium to the carbazole-1,4-quinone (3) provided carbazomycin G (1).

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