One-Step Synthesis of 1,3,4-Oxadiazines, 4,5,6,7-Tetrahydro-1h-Indoles, and Functionalized Benzo[B]Carbazoles Catalyzed by Rare Earth Metal Triflates and Cooperative Enamine-Bronsted Acid DOI Open Access

Jose Cortes Vazquez

Published: May 1, 2023

Design and development of novel one-step reactions that produce nitrogen-containing scaffolds is an invaluable area chemistry due to the abundance these moieties in natural products biologically active molecules. Discovering methods using uncommon substrates rare earth metals access significant present a challenge. Over course my doctoral studies, I have designed, developed optimized by rarely known afforded important scaffolds. The obtained allow otherwise long-to-synthesize molecules expeditious construction

Language: Английский

Prediction of the reaction mechanisms of sesquiterpene coumarin synthases supports a direct evolutionary link with triterpene biosynthesis. DOI Open Access
Michael J. Stephenson, Peter E. Brodelius

bioRxiv (Cold Spring Harbor Laboratory), Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Abstract Sesquiterpene coumarins are primarily produced by plants of the Apiaceae and Asteraceae families. Farnesylation 7-hydroxycoumarins such as umbelliferone, scopoletin or isofraxidin yield linear 7-farnesyloxycoumarins that converted to various cyclic sesquiterpene coumarin synthases (cyclases). The terminal double bond is epoxidized a epoxidase. diverse 7-(10′,11′-oxidofarnesyloxy)-coumarins protonated generate carbocation initiates cyclization farnesyl moiety (A process analogous cascades observed with other cyclases involved in biosynthesis additional terpene classes, triterpenes). These reaction mechanisms typically include Wagner-Meerwein rearrangements, hydride, methyl, alkyl shifts, but can also involve more complex processes including Grob fragmentations. Around 260 based on have been described, essentially nothing known about biosynthetic enzymes involved, i.e ., farnesyltransferase, epoxidase synthase. In this review, putative pathways for formation carbon skeletons all 7-farnesyloxycoumarins-derived presented.

Language: Английский

Citations

0
Computational studies on the sterol-like cyclization of a monodomain class II terpene cyclase DOI
B. Andes Hess,

Jörn Piel,

Lidia Smentek

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(48), P. 10647 - 10651

Published: Jan. 1, 2021

Delineation of the mechanism with DFT calculations.

Language: Английский

Citations

1
Protonating Enzymes to Access Chiral Compounds DOI
Julian Ludwig, Natalie Härterich, Bernhard Hauer

et al.

Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 305 - 311

Published: Aug. 24, 2023

Language: Английский

Citations

0
One-Step Synthesis of 1,3,4-Oxadiazines, 4,5,6,7-Tetrahydro-1h-Indoles, and Functionalized Benzo[B]Carbazoles Catalyzed by Rare Earth Metal Triflates and Cooperative Enamine-Bronsted Acid DOI Open Access

Jose Cortes Vazquez

Published: May 1, 2023

Design and development of novel one-step reactions that produce nitrogen-containing scaffolds is an invaluable area chemistry due to the abundance these moieties in natural products biologically active molecules. Discovering methods using uncommon substrates rare earth metals access significant present a challenge. Over course my doctoral studies, I have designed, developed optimized by rarely known afforded important scaffolds. The obtained allow otherwise long-to-synthesize molecules expeditious construction

Language: Английский

Citations

0