The chemistry and biology of febrifugine and halofuginone

NP McLaughlin, P Evans, M Pines - Bioorganic & Medicinal Chemistry, 2014 - Elsevier
Abstract The trans-2, 3-disubstituted piperidine, quinazolinone-containing natural product
febrifugine (also known as dichroine B) and its synthetic analogue, halofuginone, possess …

Chemical synthesis of febrifugine and analogues

S Smullen, NP McLaughlin, P Evans - Bioorganic & Medicinal Chemistry, 2018 - Elsevier
Abstract The quinazolinone-containing 2, 3-disubstituted piperidines febrifugine and
isofebrifugine have been the subject of significant research efforts since their occurrence in …

Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)-and (−)-febrifugine and halofuginone

NP McLaughlin, P Evans - The Journal of organic chemistry, 2010 - ACS Publications
The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for
the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This …

Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts

C Zhong, Y Wang, AW Hung, SL Schreiber… - Organic …, 2011 - ACS Publications
An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to
result in 3, 5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were …

BF3· Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N, O-acetal with silyl enol ether and application to the asymmetric synthesis of (+) …

RC Liu, W Huang, JY Ma, BG Wei, GQ Lin - Tetrahedron Letters, 2009 - Elsevier
The asymmetric BF3· Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N, O-
acetal 10 with silyl enol ethers derived from ketones are described.(+)-Febrifugine 1, an …

Synthesis of Substituted Morpholines Using Stereodivergent Aza-Michael Reactions Catalyzed by Brønsted Acids

C Zhong, Y Wang, C O'Herin, DW Young - ACS Catalysis, 2013 - ACS Publications
A diastereoselective intramolecular aza-Michael reaction between N-Cbz carbamates and
enones was studied. The investigation revealed that Brønsted acids with different strengths …

Sodium borohydride or potassium carbonate-mediated intramolecular Michael addition: a general method for the synthesis of fused dihydrofuran and furan derivatives

S Samanta, R Jana, JK Ray - Tetrahedron Letters, 2009 - Elsevier
A simple and convenient method for the synthesis of fused dihydrofuran derivatives using
NaBH4-mediated reductive cyclization and fused furan derivatives by K2CO3-mediated …

An asymmetric synthesis of febrifugine, halofuginone and their hemiketal isomers

S Smullen, P Evans - Tetrahedron, 2017 - Elsevier
A new synthesis of both enantiomers of naturally occurring febrifugine (1) and its analogue
halofuginone (3) are reported. This robust route relies on an enzymatic kinetic resolution …

Complementary chemoenzymatic routes to both enantiomers of febrifugine

MA Wijdeven, RJF van den Berg, R Wijtmans… - Organic & …, 2009 - pubs.rsc.org
Two complementary strategies for the synthesis of febrifugine are detailed based on
previously developed chemoenzymatic approaches to the 3-hydroxypiperidine skeleton …

Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

M Kissane, M Murphy, E O'Brien, J Chopra… - Organic & …, 2011 - pubs.rsc.org
Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and
selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described …