Le compose du titre peut etre synthetise par hydrolyse de l'acide dichloroiodoso-2 cyclopropanecarboxylique; la base associee a l'acide obtenu est un nucleophile qui par action sur le (diphenyl nitro-4 phenyl) phsophate provoque la coupure de celui-ci;des calculs ab initio sont effectues sur le compose du titre
Enantioselective Cyclopropanation of Allylic Alcohols with Dioxaborolane Ligands: Scope and Synthetic Applications
作者:André B. Charette、Hélène Juteau、Hélène Lebel、Carmela Molinaro
DOI:10.1021/ja982055v
日期:1998.11.1
the conversion of allylicalcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extended with success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. The cyclopropanation of allylic carbamates has also
Two practical and complementary methods are reported for the synthesis of trifluoromethylated alkynes. The first one, a mix‐and‐stir process, is based on the oxidative trifluoromethylation of readily available and bench‐stable copper acetylides while the second one, which displays a broad substrate scope and has several advantages over existing procedures, is based on the oxidativecopper‐catalyzed
Highly Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes by Using α-Iodo- and α-Chloromethylzinc Carbenoids
作者:Louis-Philippe B. Beaulieu、Lucie E. Zimmer、Alexandre Gagnon、André B. Charette
DOI:10.1002/chem.201202528
日期:2012.11.12
α‐chlorozinc carbenoids by using a dioxaborolane‐derived chiral ligand. The synthetically useful iodocyclopropane building blocks were derivatized by an electrophilic trapping of the corresponding cyclopropyl lithium species or a Negishi coupling to give access to a variety of enantioenriched 1,2,3‐substituted cyclopropanes. The synthetic utility of this method was demonstrated by the formal synthesis of an
Streamlined Symmetrical Total Synthesis of Disorazole B<sub>1</sub> and Design, Synthesis, and Biological Investigation of Disorazole Analogues
作者:K. C. Nicolaou、Johannes Krieger、Ganesh M. Murhade、Parthasarathi Subramanian、Balu D. Dherange、Dionisios Vourloumis、Stefan Munneke、Baiwei Lin、Christine Gu、Hetal Sarvaiaya、Joseph Sandoval、Zhaomei Zhang、Monette Aujay、James W. Purcell、Julia Gavrilyuk
DOI:10.1021/jacs.0c07094
日期:2020.9.9
naturally occurring disorazole B1 molecule, a symmetrical totalsynthesis was devised with a monomeric advanced intermediate as the key building block, whose three-step conversion to the natural product allowed for an expeditious entry to this family of compounds. Application of the developed synthetic strategies and methods provided a series of designed analogues of disorazole B1, whose biological evaluation
Syntheses of Cyclopropyl Analogues of Disorazoles A<sub>1</sub> and B<sub>1</sub> and Their Thiazole Counterparts
作者:K. C. Nicolaou、Marek Buchman、Gabriel Bellavance、Johannes Krieger、Parthasarathi Subramanian、Kiran Kumar Pulukuri
DOI:10.1021/acs.joc.8b02137
日期:2018.10.19
Modular syntheses of disorazoles A1 and B1 analogues in which the epoxide moieties of the natural products were replaced with cyclopropyl units have been achieved. Targeted as part of a structure–activity relationships study, these syntheses were successfully extended to the thiazole counterparts of these analogues. The retrosynthetically defined fragments were assembled through Yamaguchi esterification