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Issue 6, 2014
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Total syntheses of indolactam alkaloids (−)-indolactam V, (−)-pendolmycin, (−)-lyngbyatoxin A, and (−)-teleocidin A-2

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Abstract

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.

Graphical abstract: Total syntheses of indolactam alkaloids (−)-indolactam V, (−)-pendolmycin, (−)-lyngbyatoxin A, and (−)-teleocidin A-2

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Article information


Submitted
24 Jan 2014
Accepted
10 Feb 2014
First published
10 Feb 2014

Chem. Sci., 2014,5, 2184-2190
Article type
Edge Article

Total syntheses of indolactam alkaloids (−)-indolactam V, (−)-pendolmycin, (−)-lyngbyatoxin A, and (−)-teleocidin A-2

N. F. Fine Nathel, T. K. Shah, S. M. Bronner and N. K. Garg, Chem. Sci., 2014, 5, 2184
DOI: 10.1039/C4SC00256C

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