Total syntheses of the marine pyrrole alkaloids polycitone A and B.
Polycitone B (2) was obtained in four steps from pyrrole dicarboxylic acid 3, including Friedel-Crafts reaction of the corresponding acid chloride with anisole. The conversion of 2 into polycitone A (1) was achieved in two steps via Mitsunobu alkylation of the pyrrolic NH group. The synthesis of polycitone A proceeds in 18% overall yield and offers the possibility of varying the substituents on the pyrrole ring.
Kreipl
Andreas T
AT
Chemie Department, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13 (Haus F), Germany.
Reid
Caroline
C
Steglich
Wolfgang
W
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D014561:Urochordata / Q000737:chemistry
D000470:Alkaloids; D011758:Pyrroles; C403044:polycitone A; C412849:polycitone B