Alain Godard

A new convergent synthesis of alpha - substituted - beta - carbolines

Abstract New convergent synthesis of natural α-substituted-β-carbolines through metalations, cross-couplings and intramolecular substitution via (2-aminobenzene)-boronic acid, arylstannanes and ortho-fluoroiodopyridines.

Convergent synthesis of the streptonigrin alkaloid skeleton. Directed orthometalation connection to aryl-aryl cross-coupling

Abstract A convergent synthesis of 2-[2-(4-phenyl-3-pivaloylamino) pyridyl]quinolines, the streptonigrin alkaloid skeleton, is reported. The methodology involves independent elaboration of the three main building blocks by metalation and two coupling reactions catalyzed by palladium.

FIRST HALOGEN-DANCE REACTION IN QUINOLINE SERIES : APPLICATION TO A NEW SYNTHESIS OF QUINDOLINE.

Abstract The first halogen-dance reaction in quinoline series is described as well as a new convergent synthesis of quindoline, a natural benzo-δ-carboline.

Convergent synthesis of streptonigrin and Lavendamycin analogues

Abstract A convergent synthesis of streptonigrin and lavendamycin analogues incorporating a quinoline-5,8-dione structure is reported. The approach is based on our synthetic methodology which involves such reactions as metalation, heteroring cross-coupling and oxidative demethylation.

A short synthesis of the antimicrobial marine sponge pigment fascaplysin.

Abstract A short and convergent synthesis of Fascaplysin is reported. The approach is based on a recently developped methodology which involves such reactions as metalation, heteroring cross-coupling and cyclization.

On the metallation of 2-isopropylpyridine

Abstract 2-Isopropylpyridine has been successfully metallated and functionalized by using potassium diisopropylamide (KDA). Subsequent functionalization has been achieved with a wide range of electrophiles and good to excellent yields have been obtained. The action of other potassium or sodium bases has also been investigated.

FIRST TOTAL SYNTHESIS OF CRYPTOMISRINE

Abstract The first total synthesis of cryptomisrine, a novel indolo[3,2-b]quinoline dimeric alkaloid from Cryptolepis sanguinolenta, is reported. The approach is based on a convergent methodology which involves a new halogen-dance reaction in quinoline series connected to a cross-coupling reaction.

Metallation in connection with cross-coupling reactions. Coupling of hindered aryls for the synthesis of 4-phenylpyridines as part of Streptonigrin and Lavendamycin analogues

Abstract The synthesis of the CD ring system of Streptonigrin and Lavendamycin alkaloid analogues by cross-coupling under Suzukis conditions has been studied. Steric hindrance is the main problem. It has been solved either by using strong bases or working in a sealed tube under pressure.

A new approach to the synthesis of lavendamycin analogues.

Abstract A three-steps approach to the lavendamycin skeleton from benzene, pyridine and quinoline blocks is described. It is based on a new synthetic methodology for the preparation of α-substituted β-carbolines which involves such reactions as Directed Ortho Metalation and Heteroring Cross-Coupling.

An original one-pot synthesis of 5-(4-pyridyl)-benzo[c]-2,7-naphthyridine as key intermediate in the synthesis of amphimedine by metalation connected with cross-coupling reaction

Abstract A short new route to 4,5-disubstituted-benzo[c]-2,7-naphthyridines has been developed. The strategy involves directed ortho metalation of pyridines following by an halogen dance reaction and biaryl cross-coupling as key steps. A concise and efficient one-pot synthesis of 4-chloro-5-(4-pyridyl)-benzo[c]-2,7-naphthyridine, as a key intermediate in the synthesis of amphimedine is described.