[HTML][HTML] Applications of Friedel–Crafts reactions in total synthesis of natural products

MM Heravi, V Zadsirjan, P Saedi, T Momeni - RSC advances, 2018 - pubs.rsc.org
Over the years, Friedel–Crafts (FC) reactions have been acknowledged as the most useful
and powerful synthetic tools for the construction of a special kind of carbon–carbon bond …

Total synthesis of the pseudoindoxyl class of natural products

PS Dhote, P Patel, K Vanka, CV Ramana - Organic & Biomolecular …, 2021 - pubs.rsc.org
The pseudoindoxyl sub-structural motif, amongst the large set of the indole class of
alkaloids, represents a unique subset of the oxygenated indole class of the alkaloid family. A …

Total syntheses of (−)-mersicarpine,(−)-scholarisine G,(+)-melodinine E,(−)-leuconoxine,(−)-leuconolam,(−)-leuconodine A,(+)-leuconodine F, and (−)-leuconodine C …

Z Xu, Q Wang, J Zhu - Journal of the American Chemical Society, 2015 - ACS Publications
Enantioselective total syntheses of title natural products from a common cyclohexenone
derivative (S)-18 were reported. Ozonolysis of (S)-18 afforded a stable diketo ester (R)-17 …

Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E …

Y Yang, Y Bai, S Sun, M Dai - Organic letters, 2014 - ACS Publications
Inspired by their potential biosynthesis, we have developed divergent total syntheses of
seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D …

Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid

M Ghosh, S Sahu, S Saha, MS Maji - Chemical Science, 2024 - pubs.rsc.org
Herein we report a branch-selective allylation strategy for accessing C2-indolyl-all-carbon
quaternary centers using allylboronic acids. This approach boasts broad functional group …

Synthesis of silafluorenes and silaindenes via silyl radicals from arylhydrosilanes: intramolecular cyclization and intermolecular annulation with alkynes

L Xu, S Zhang, P Li - Organic Chemistry Frontiers, 2015 - pubs.rsc.org
Intramolecular homolytic aromatic silylation of biphenyl-2-hydrosilanes via silyl radicals has
been developed for the synthesis of silafluorenes. Moreover, silaindenes are synthesized …

Total syntheses of leuconoxine, leuconodine B, and melodinine E by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

A Umehara, H Ueda, H Tokuyama - Organic letters, 2014 - ACS Publications
Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a
divergent route. The [5.5. 6.6] diazafenestrane skeleton was constructed from an indole-3 …

Evolution of biocatalytic and chemocatalytic C–H functionalization strategy in the synthesis of manzacidin C

CR Zwick III, H Renata - The Journal of Organic Chemistry, 2018 - ACS Publications
Because of their unique molecular architecture, the manzacidins have been the subject of
intense synthetic efforts in the past two decades. Here, we describe two synthetic …

DMSO/SOCl2-Enabled Synthesis of 3-Chloroindoles via Desulfonylative Chlorocyclization of N,N-Disubstituted 2-Alkynylanilines

X Li, Y Cheng, Y Li, F Sun, X Zhan, Z Yang… - The Journal of …, 2024 - ACS Publications
The application of the DMSO/SOCl2 system enabled the intramolecular
cyclization/chlorination of N, N-disubstituted 2-alkynylanilines, leading to the synthesis of a …

Total Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through a Radical Translocation–Cyclization Cascade

R Kim, AJ Ferreira, CM Beaudry - Angewandte Chemie, 2019 - Wiley Online Library
The Aspidosperma alkaloids leuconoxine, melodinine E, and mersicarpine were
synthesized. The approach features a key cascade radical reaction. A 1, 5‐hydrogen atom …