Michel Journet

Highly efficient synthesis of α,β-acetylenic aldehydes from terminal alkynes using DMF as the formylating reagent

Abstract The formylation of lithium acetylides with DMF led to α,β-acetylenic aldehydes in excellent yields (>94%). A reverse quench into a phosphate buffer (10% aqueous KH 2 PO 4 ,4 equiv) proved to be the key for this high-yielding reaction.

Highly efficient and mild synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives

Abstract Synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives 2 was accomplished by reacting sodium azide with α,β-acetylenic aldehydes 1 in DMSO at room temperature. Therefore, the reaction remains basic avoiding the generation of the hazardous explosive HN 3 , resulting in a safe process. This mild and general reaction was instantaneous and was essentially quantitative.

Highly Efficient Synthesis of HIV NNRTI Doravirine

The development of an efficient and robust process for the production of HIV NNRTI doravirine is described. The synthesis features a continuous aldol reaction as part of a de novo synthesis of the key pyridone fragment. Conditions for the continuous flow aldol reaction were derived using microbatch snapshots of the flow process.

AN IMPROVED AND PRACTICAL PROCEDURE FOR THE SYNTHESIS OF SUBSTITUTED PHENYLACETYLPYRIDINES

Abstract A general procedure for the synthesis of substituted phenylacetylpyridines in excellent yields is described using a Horner-Emmons condensation between α-aminoalkylphosphonates of pyridinecarboxaldehydes and benzaldehydes with cesium carbonate at room temperature.

A general method for the highly diastereoselective, kinetically controlled alkylation of (+)-nopinone

Abstract A general method for the monoalkylation of (+)-nopinone was developed for a variety of carbon and heteroatom electrophiles to afford the kinetically controlled product 2 with high diastereoselectivity (98% d.e.) and excellent yield (75–90%).

Diastereoselective triple radical cyclization of a bromomethyldimethylsilyl allyl ether

Abstract A convergent strategy to construct the B-ring in an AC → ABC cyclization to the taxane framework was tested. The bicyclic bromomethyldimethylsilyl ether 2 was efficiently synthesized by a sequence proceeding through the alkylation of the C-ring malonate 4 by the hindered A-ring bromide 3 . The desired tandem 5-exo-trig/8-exo-dig cyclization of 2 to diol 1 was not observed. An alternative pathway was indicated by isolation of crystalline tetracyclic diastereomers 12a and 12b , derived by a diastereoselective sequence of three radical cyclizations.