Nine-step enantioselective total synthesis of (−)-vincorine

BD Horning, DWC MacMillan - Journal of the American Chemical …, 2013 - ACS Publications
A concise and highly enantioselective total synthesis of the akuammiline alkaloid (−)-
vincorine has been accomplished. A key element of the synthesis is a stereoselective …

Total synthesis of akuammiline alkaloid (−)-vincorine via intramolecular oxidative coupling

W Zi, W Xie, D Ma - Journal of the American Chemical Society, 2012 - ACS Publications
An asymmetric total synthesis of the Akuammiline alkaloid (−)-vincorine (18 steps from 5-
methoxytryptamine, 5% overall yield) is described. The key steps include Pd-catalyzed direct …

Total Synthesis of the Akuammiline Alkaloid (±)-Vincorine

M Zhang, X Huang, L Shen, Y Qin - Journal of the American …, 2009 - ACS Publications
The first total synthesis of the akuammiline alkaloid (±)-vincorine (6) has been accomplished
in about 1% overall yield in 31 steps. A concise assembly of the core 1, 2-disubstituted 1, 2 …

Enantioselective total syntheses of methanoquinolizidine-containing akuammiline alkaloids and related studies

E Picazo, LA Morrill, RB Susick, J Moreno… - Journal of the …, 2018 - ACS Publications
The akuammiline alkaloids are a structurally diverse class of bioactive natural products
isolated from plants found in various parts of the world. A particularly challenging subset of …

Total synthesis of the Strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck− iminium ion cyclization

AB Dounay, PG Humphreys, LE Overman… - Journal of the …, 2008 - ACS Publications
A 1, 2, 3, 4-tetrahydro-9a, 4a-(iminoethano)-9 H-carbazole (4) is a central structural feature
of the Strychnos alkaloid minfiensine (1) and akuammiline alkaloids such as vincorine (5) …

Total synthesis of (−)‐Vindorosine

W Chen, XD Yang, WY Tan, XY Zhang… - Angewandte Chemie …, 2017 - Wiley Online Library
Outlined herein is a novel and scalable synthesis of (−)‐vindorosine based on two key
transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone …

Asymmetric total synthesis of (+)-apovincamine and a formal synthesis of (+)-vincamine. Demonstration of a practical “asymmetric linkage” between aromatic …

AG Schultz, WP Malachowski… - The Journal of Organic …, 1997 - ACS Publications
Asymmetric syntheses of (+)-apovincamine (1a) and (+)-vincamine (2) are described.
Construction of the pentacyclic diene lactam 14, a pivotal intermediate for synthesis of the …

A general Iridium-catalyzed reductive dienamine synthesis allows a five-step synthesis of catharanthine via the elusive dehydrosecodine

P Gabriel, YA Almehmadi, ZR Wong… - Journal of the American …, 2021 - ACS Publications
A new reductive strategy for the stereo-and regioselective synthesis of functionalized
isoquinuclidines has been developed. Pivoting on the chemoselective iridium (I)-catalyzed …

Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine

B Scheiper, F Glorius, A Leitner… - Proceedings of the …, 2004 - National Acad Sciences
A concise and efficient total synthesis of the spermidine alkaloid (-)-isooncinotine
incorporating a 22-membered lactam ring is outlined. The approach is largely catalysis …

Efficient syntheses of (−)-crinine and (−)-aspidospermidine, and the formal synthesis of (−)-minfiensine by enantioselective intramolecular dearomative cyclization

K Du, H Yang, P Guo, L Feng, G Xu, Q Zhou… - Chemical …, 2017 - pubs.rsc.org
Polycyclic alkaloids bearing all-carbon quaternary centers possess a diversity of biological
activities and are challenging targets in natural product synthesis. The development of a …