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

Опубликована: Май 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

Язык: 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), Год журнала: 2024, Номер unknown

Опубликована: Окт. 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.

Язык: Английский

Процитировано

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

Jörn Piel,

Lidia Smentek

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(48), С. 10647 - 10651

Опубликована: Янв. 1, 2021

Delineation of the mechanism with DFT calculations.

Язык: Английский

Процитировано

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

и другие.

Elsevier eBooks, Год журнала: 2023, Номер unknown, С. 305 - 311

Опубликована: Авг. 24, 2023

Язык: Английский

Процитировано

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

Опубликована: Май 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

Язык: Английский

Процитировано

0