Pierre Grandclaudon

An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and Horner reaction of o-(and m-)halogeno-N-phosphorylmethylbenzamide derivatives

Abstract A series of 3-(alkyl and aryl)methylene-2,3-dihydro-1 H -isoindol-1-one derivatives was synthesized by a one-pot reaction sequence involving lithiation of 2- (or 3-)halogeno- N -phosphorylmethylbenzamides, cyclization of the aryne intermediate, metal migration and Horner reaction of the resulting phosphorylated aminocarbanion with selected aromatic and aliphatic aldehydes.

A New Approach to Isoindolobenzazepines. A Simple Synthesis of Lennoxamine

Abstract A convenient and versatile short-step synthesis of isoindolobenzazepines, illustrated by a total synthesis of the alkaloid lennoxamine 1 , is described.

LDA-INDUCED METALATION OF ISOINDOLINONES. AN EFFICIENT ROUTE TO 3-SUBSTITUTED ISOINDOLINE DERIVATIVES

Abstract 3-Substituted isoindolines have been efficiently prepared by sequential lithiation and reduction of isoindolinones.

First total synthesis of fumaridine

Abstract The first total synthesis of the alkaloid fumaridine 1a is reported. The key step is the assemblage of the arylmethylene isoindolinone 2a (E) by Horner reaction between the phosphorylated isoindolinone 3a and the suitably substituted benzaldehyde 4 . N-Lactam deprotection and concomitant E→Z isomerization complete the synthesis of the title compound.

Diastereoselective addition of metalated isoindolin-1-ones to aldehydes. Stereoselective preparation of (E)-3-arylideneisoindolin-1-ones

Lithiated isoindolinones react with aromatic aldehydes to afford 3-hydroxybenzyl derivatives with high diastereoselectivity. Dehydration of erythro and threo adducts through an E1cb mechanism gives rise indiscriminately to the (E)-arylideneisoindolinones.

TOTAL SYNTHESES OF ()-CRYPTOPLEURINE, ()-ANTOFINE AND ()-DEOXYPERGULARININE

Abstract The alkaloids (±)-cryptopleurine 1 , (±)-antofine 2 , and (±)-deoxypergularinine 3 were synthesized by Pictet-Spengler cyclization of the 2-arylmethylpiperidine and -pyrrolidines 4, 5 and 6 obtained by sequential N -deprotection-reduction of the parent enecarbamates 7, 8 and 9 . These latter were made by the Horner reaction of phosphorylated carbamates 12 and 13 with the appropriate aldehydes 10 and 11 .

A new synthetic route to highly enantioenriched 3-substituted-2,3-dihydro-1H-isoindol-1-ones

Abstract A concise and efficient synthesis of highly enantioenriched 3-alkyl and 3-aryl-2,3-dihydro-1H-isoindolinones is reported. The key step relies on the diastereoselective reduction of the N-acylhydrazonium salts generated by acidic treatment of hemiaminal precursors bearing the (S)-2-methoxymethylpyrrolidin-1-yl (SMP) auxiliary.

Synthesis and Biological Evaluation of Aristolactams

A variety of aristolactam derivatives were synthesized and evaluated for cytotoxicity. Modulations were carried out on the phenanthrene nucleus and the lactam moiety as well. N-(N-dialkylaminoalkyl) derivatives exhibited interesting cytotoxic activity against the L1210 leukemia cell line.

A convenient synthesis of enamides and dienamides by Horner-Wittig and Wadsworth-Emmons reactions

Abstract Various N-acyl-N-alkyl-1-amino-alkenes and −1,3-dienes have been efficiently prepared by reacting aldehydes or ketones 3 with N-alkyl-N-(diphenylphosphinoyl)methyl and −N-(diethoxyphosphoryl)methyl carboxamides 1, 2 .

A new synthetic route to 2-alkyl-4-aryl-1(2H)-isoquinolones and 2-alkyl-4-aryl-1,2,3,4-tetrahydroisoquinolines

Abstract 4-Aryl and heteroaryl-1(2 H )-isoquinolones have been prepared by base promoted cyclization of phosphorylated o -aroyl and heteroaroyl benzamides. Subsequent reduction of the carbonyl and styryl functions of the annulated products has given rise to 4-aryl-1,2,3,4-tetrahydroisoquinolines.