Total synthesis of carbazoquinocin C: application of the o-benzannulation of Fischer carbene complexes to carbazole-3,4-quinone alkaloids.
[reaction: see text] The photoinduced o-benzannulation of 3-(2-vinyl)indolylcarbene complexes provides a direct route to carbazole derivatives that are oxygenated in the 3- and 4-positions. This reaction is quite efficient and provides for a unique synthesis of the lipid peroxidation inhibitor carbazoquinocin C.
Rawat
Manish
M
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Wulff
William D
WD
D000470:Alkaloids / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D016227:Benzoquinones; D002227:Carbazoles; D011809:Quinones; C485127:carbazoquinocin C; C041514:carbazole; C004532:quinone