Henri-Philippe Husson
Institut de Chimie des Substances Naturelles
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Featured researches published by Henri-Philippe Husson.
Phytochemistry | 1989
Elisabeth Davioud; Christiane Kan; Janine Hamon; Jacques Tempé; Henri-Philippe Husson
Abstract Following in vitro infection of an aseptic Catharanthus trichophyllus plant with Agrobacterium rhizogenes (15834), six hairy root cultures were established. These were compared with normal root cultures, derived from the same plant, with respect to production of indole alkaloids. A rapidly growing hairy root line was used for fermenter (201) cultures. The alkaloid content of the roots obtained was examined. Seventeen monomeric indole alkaloids were purified and characterized, including five hitherto undescribed substances. Normal root and hairy root line cultures showed similar alkaloid composition. Analyses, performed at five-week intervals on five-week-old cultures showed variable alkaloid yields.
Tetrahedron Letters | 1982
Martine Bonin; José R Romero; David S. Grierson; Henri-Philippe Husson
The cis 2,6-dialkylpiperidine alkaloid (±) dihydro-pinidine 7b and the trans alkaloid (±) solenopsin A 5a were synthesized from a common α-aminonitrile synthon 1. The key step in this synthesis was the stereoselective reductive decyanation of the 1-benzyl-2cyano-2′, 6-dialkylpiperidines 3a and 3b.
Tetrahedron Letters | 1985
Jacques Royer; Henri-Philippe Husson
Abstract The first enantiospecific synthesis of the indolizidine alkaloid (−) gephyrotoxin-223 AB 2 has been achieved from the chiral 2-cyano-6-oxazolopiperidine synthon 3 .
Tetrahedron Letters | 1998
Isabelle Cabanal-Duvillard; Jean-François Berrien; Jacques Royer; Henri-Philippe Husson
Bromination and bromohydroxylation of oxazolidinones derived from cyclohexadiene have been studied in order to synthetize (±)-epibatidine 19. Bromohydroxylation of compound 2 led to a polyfunctionalized halohydrin 11a which could be further cyclized to azabicyclo[2.2.1]heptan-2-one 16 already described as a precursor of epibatidine 18.
Tetrahedron | 1997
Catherine Maury; Qian Wang; Tawfik Gharbaoui; Mohamed Chiadmi; Alain Tomas; Jacques Royer; Henri-Philippe Husson
Abstract Two strategies have been developed to synthesize both enantiomers of piperidin-2-yl-phosphonic acid. The first one uses the double condensation of glutaraldehyde with ( R )-(−)-phenylglycinol and triethylphosphite to give 2-ethylphosphonate-6-oxazolopiperidine 2 which furnished in few steps ( S )-(+)-piperidin-2yl-phosphonic acid ( 5 ) in 58% ee. The second strategy utilizes the 2-cyano-6-oxazolopiperidine synthon 1 which upon treatment with trimethyl phosphite gave 2-cyano-6-oxazaphosphorinane 7 which gave pure ( R )-(−)-piperidin-2-yl-phosphonic acid ( 10 ) in good overall yield.
Tetrahedron Letters | 1992
Catherine Maury; Jacques Royer; Henri-Philippe Husson
Abstract A simple and general method for the asymmetric synthesis of α-aminophosphonic acids is described. A chiral phosphonate prepared in one step from R-(−)-phenylglycinol was alkylated with good diastereoselectivity using different electrophiles.
Tetrahedron Letters | 1994
Isabelle Baussanne; Angèle Chiaroni; Henri-Philippe Husson; Claude Riche; Jacques Royer
Abstract A new chiral non-racemic γ-lactam 1 easily prepared in one step from ( R )-(−)-phenylglycinol was bis-alkylated α to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.
Tetrahedron Letters | 1988
Jean-Charles Quirion; David S. Grierson; Jacques Royer; Henri-Philippe Husson
Abstract The enantiospecific synthesis of (+) and (−) isonitramines 7 has been achieved from a common chiral intermediate 5 ; this key compound was formed by condensation of two molar equivalents of glutaraldehyde with one mole of (−) phenylglycinol.
Tetrahedron Letters | 1987
Françoise Tubéry; David S. Grierson; Henri-Philippe Husson
Abstract The simple 5,6-dihydropyridinium salt 2 (R 1 = CH 3 ′ R 2-5 = H) was prepared by reaction of the Δ 2 piperidone 1 (obtained from 3 ; 85% overall yield) with acetyl chloride at −50°C. Reaction of 2 with Grignard reagents gave the C-2 substituted products 6 a-f. Compound 6e was converted in three simple steps to the benzomorphan 12 .
Tetrahedron Letters | 1985
José L. Marco; Jacques Royer; Henri-Philippe Husson
The synthesis of (−)-N-Cyanomethyl-4-phenyl-1,3-oxazolidine 1 is reported. Good yields and moderate diastereomeric excesses (d.e.s.) of mono- and di-substituted α-aminonitriles were obtained from this simple chiral template.