A concise synthesis of topsentin A and nortopsentins B and D.
[reaction: see text] A concise synthesis of topsentin A (R(1) = R(2) = H) and nortopsentins B (R(1) = Br, R(2) = H) and D (R(1) = R(2) = H) is described from oxotryptamine 5 via reduction of acyl cyanide 4. Regiospecific bromination of 3-cyanoindole afforded 6-bromo-3-cyanoindole (10) as the major product.
Miyake
F Y
FY
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.
Yakushijin
K
K
Horne
D A
DA
D000818:Animals; D007093:Imidazoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry*
D007093:Imidazoles; D007202:Indicators and Reagents; D007211:Indoles; C413129:topsentin A; C070184:topsentin