Strategies for the formation of tetrahydropyran rings in the synthesis of natural products

PA Clarke, S Santos - European journal of organic chemistry, 2006 - Wiley Online Library
This microreview surveys the literature over the last five years with regard to construction of
functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products …

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

A Budakoti, PK Mondal, P Verma… - Beilstein Journal of …, 2021 - beilstein-journals.org
Functionalized tetrahydropyran (THP) rings are important building blocks and ubiquitous
scaffolds in many natural products and active pharmaceutical ingredients (API). Among …

[PDF][PDF] Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond-forming reactions

I Larrosa, P Romea, F Urpí - Tetrahedron, 2008 - academia.edu
Six-membered oxygenated heterocycles, or pyrans, are probably one of the most common
structural motifs spread across natural products, from simple glucose to structurally complex …

[PDF][PDF] Allylboration of carbonyl compounds

H Lachance, DG Hall - ChemInform, 2010 - medien.umbreitkatalog.de
Allylic boron compounds have gained a prominent position as a useful class of synthetic
reagents in the past 25 years. Their general structures, 1 and 2, and their utility in carbonyl …

Direct access to monoprotected homoallylic 1, 2-diols via dual chromium/photoredox catalysis

F Schäfers, L Quach, JL Schwarz, M Saladrigas… - ACS …, 2020 - ACS Publications
Herein, we present a dual catalytic strategy to efficiently obtain monoprotected homoallylic 1,
2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct …

A boron alkylidene–alkene cycloaddition reaction: application to the synthesis of aphanamal

X Liu, TM Deaton, F Haeffner… - Angewandte Chemie, 2017 - Wiley Online Library
We describe an unusual net [2+ 2] cycloaddition reaction between boron alkylidenes and
unactivated alkenes. This reaction provides a new method for the construction of carbocyclic …

Stereocontrolled Total Synthesis of (+)‐Altohyrtin A/Spongistatin 1

I Paterson, DYK Chen, MJ Coster… - Angewandte Chemie …, 2001 - Wiley Online Library
First reported in 1993 by three groups (Kobayashi and Kitagawa, Pettit, and Fusetani),[1] the
altohyrtins/spongistatins/cinachyrolides are a unique family of antimitotic macrolides [2±5] …

Completely OH-Selective FeCl3-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans

K Zheng, X Liu, S Qin, M Xie, L Lin, C Hu… - Journal of the American …, 2012 - ACS Publications
The completely OH-selective Prins cyclization has been realized from the enantioselective
ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated …

Natural products containing oxygen heterocycles—Synthetic advances between 1990 and 2015

J Cossy, A Guerinot - Advances in Heterocyclic Chemistry, 2016 - Elsevier
Oxygen-containing heterocycles are ubiquitous in biologically active natural products, which
can be a great source of inspiration in drug discovery. Due to the importance of this class of …

α-Hydroxyallylation Reaction of Carbonyl Compounds

M Lombardo, C Trombini - Chemical reviews, 2007 - ACS Publications
The stereoselective synthesis of carbohydrates and related bioactive compounds containing
a polyhydroxylated chain embedded in their structural framework remains a topic of great …