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
BIOSYNTHESIS OF INDOLE ALKALOID TUMOR PROMOTERS TELEOCIDINS (I) POSSIBLE BIOSYNTHETIC PATHWAY OF THE MONOTERPENOID MOIETIES OF TELEOCIDINS
Irie, Kazuhiro,Kajiyama, Shin-ichiro,Funaki, Atsushi,Koshimizu, Koichi,Hayashi, Hideo,Arai, Motoo
, p. 2773 - 2788 (2007/10/02)
Possible biosynthetic pathway of monoterpenoid moieties of teleocidins shown in Fig. 8 was proposed by feeding experiments with several D or 13C-labelled precursors and isolation of new telecidin-related metabolites named blastmycetin D (6) and E (7).