119375-01-8Relevant articles and documents
Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2
Fine Nathel, Noah F.,Shah, Tejas K.,Bronner, Sarah M.,Garg, Neil K.
, p. 2184 - 2190 (2014/05/20)
We report the total syntheses of (-)-indolactam V and the C7-substituted indolactam alkaloids (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2. The strategy for preparing indolactam V relies on a distortion-controlled indolyne functionalization reaction to establish the C4-N linkage, in addition to an intramolecular conjugate addition to build the conformationally-flexible nine-membered ring. The total synthesis of indolactam V then sets the stage for the divergent synthesis of the other targeted alkaloids. Specifically, late-stage sp2-sp3 cross-couplings on an indolactam V derivative are used to introduce the key C7 substituents and the necessary quaternary carbons. These challenging couplings, in addition to other delicate manipulations, all proceed in the presence of a basic tertiary amine, an unprotected secondary amide, and an unprotected indole. Thus, our approach not only enables the enantiospecific total syntheses of four indolactam alkaloids, but also serves as a platform for probing complexity-generating and chemoselective transformations in the context of alkaloid total synthesis. This journal is the Partner Organisations 2014.
The Second Generation Synthesis of a Tumor Promoter Pendolmycin
Okabe, Kazuaki,Natsume, Mitsutaka
, p. 7615 - 7624 (2007/10/02)
Total synthesis of a tumor promoter pendolmycin (1) was accomplished in the stereospecific manner using a D-serine derivative 7 and an L-valine derivative 16 as chiral sources.Methyl 2-(bromomethyl)benzoate was used for the critical step of the indole cyc
Total synthesis of indole alkaloid pendolmycin
Okabe, Kazuaki,Muratake, Hideaki,Natsume, Mitsutaka
, p. 5113 - 5120 (2007/10/02)
The teleocidin class of an indole alkaloid, pendolmycin (1) was synthesized from 1-(4-methylphenylsulfonyl)pyrrole in thirteen steps by way of the indole derivative (16), the amino- diester compound (6), and the ethyl carboxylate (5).
