P stereospecific synthesis

Krapcho, A. P., Mundy, B. P. Stereospecific synthesis of 2-isopropylidene-cis,cis-4,8-dimethyl-6-keto-cis-decahydroazulene. Tetrahedron 1970, 26, 5437-5446. 

McCarthy, J.R., Huber, E.W., Le, T.-B., Laskovics, M.R, and Matthews, D.P., Stereospecific synthesis of 1-fluoro olefins via (fluorovinyl)stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry. Tetrahedron, 52, 45, 1996. 

Wipf, P. and Miller, C.P., Stereospecific synthesis of peptide analogs with aUo-threonine and D-aUo-threonine residues,/. Org. Chem. 58,1575, 1993. 

Doucet, C. Vergely, I. Reboud-Ravaux, M. Guilhem, J. Kobaiter, R. Joyeau, R. Wakselman, M. Inhibition of human leucocyte elastase by functionalized V-aryl azeti-din-2-ones. Stereospecific synthesis and chiral recognition of disymmetrically C3-substi-tuted P-lactams. Tetrahedron Asymmetry 1997, 8, 739-751. 

The most important and widely used approach to chiral sulfoxides is the method developed by Andersen (5) based on the reaction between the diastereomerically pure (or strongly enriched in one dia-stereomer) menthyl arenesulfinates and Grignard reagents. The first stereospecific synthesis of optically active (+H7 )-ethyl p-tolyl sulfoxide 22 was accomplished in 1962 by Andersen (75) from (-)-(iS)-menthyl p-toluenesulfmate 45 and ethylmagnesium iodide. 

Menthyl p-toluenesulfinate 45, a key compound in the stereospecific synthesis of sulfoxides, was also found to be a very convenient starting material for chiral sulfinamides. Montanari... 

An alternative stereospecific synthesis of chiral sulfimides reported by Nudelman (137) consists of the reaction of the diastereomeric menthyl p-toluenesulfinimidoates 90 with Gri ard reagents giving the optically active sulfimide 91. This reaction, like the Andersen synthesis of chiral sulfoxides, proceeds with inversion of configura-... 

Hodosi, G. Kovac, P., Glycosylation via locked anomeric configuration stereospecific synthesis of oligosaccharides containing the beta-D-mannopyranosyl and beta-L-rhamnopyranosyl linkage. Carbohydr. Res. 1998, 308, 63-75. 

White et al. developed a stereospecific synthesis of Z-olefins, including isotretinoin [84]. Thus, isotretinoin was obtained by a Reformatsky reaction of p-cyclocitral with the C5 bromoester, followed by DIBAL-H lactone reduction, lactol ring opening, selective olefin bond formation with ethyl 4-diethoxyphosphoryl-3-methyl-2-butenoate and further saponification, Fig. (46). 

T. T. Thang, M. de Los Angeles Laborde, A. Olesker, and G. Lukaes, A new approach to the stereospecific synthesis of branched-chain sugars, J. Chem. Soc. Chem. Commun. p. 1581... 

R. Roy and F. Tropper, Stereospecific synthesis of aryl p-D-lV-acetylglucopyranosides by phase transfer catalysis, Synth. Commun. 20 2097 (1990). 

Young, D. W. Stereospecific Synthesis of Tritium Labelled Organic Compounds using Chemical and Biological Methods, Vol. 4, p. 177, ibid. 1978... 

E. P. Barrette and L. Goodman, Convenient and stereospecific synthesis of deoxy sugars. Reductive displacement of trifluoromethylsulfonates, J. Org. Chem., 49 (1984) 176-178. 

G. Fronza, C. Fuganti, P. Grasselli, G. Pedrocchi-Fantoni, and C. Zirotti, On the steric course of the addition of diallylzinc onto a,P-dialkoxy chiral carbonyl compounds Stereospecific synthesis of 2,6-dideoxysugars of the L-series, Tetrahedron Lett., 23 (1982) 4143 1146. 

S. Oscarson and F. W. Sehgemleble, A novel p-directing fructofuranosyl donor concept. Stereospecific synthesis of sucrose, J. Am. Chem. Soc., 122 (2000) 8869-8872. 

P. L. Armstrong, I. C. Coull, A. T. Hewson, and M. J. Slater, An unusually facile [3,3]sigmatropic rearrangement in a stereospecific synthesis of novel 2, 3 -dideoxynucleo-side precursors, Tetrahedron Lett., 36 (1995) 4311—4314. 

We have studied the reaction of methyl trifluoromethanesul-fonate (methyl triflate) with isopropyl methylphosphinate (1), and have used this system to develop a new procedure for the stereospecific synthesis of trivalent (P ) organophosphorus esters. 

Testa B, Jenner P (1976) Drug metabolism chemical and biochemical aspects. Part II Biochemical aspects of drug oxidation. In Swarbrick J (ed) Drug and the pharmaceutical science. Marcel Dekker, New York, pp 271-312 Wittman MD, Kadow JK, Vyas DM (2000) Stereospecific synthesis of the major human metabolite of paclitaxel. Tetrahedron Lett 41 4729... 

Analogous to the method of van Tamelen (Volume VII, p. 51) and following that due to Corsano and Panizzi (25), a stereospecific synthesis of dl-yohimbane has been achieved (17) as shown in the sequence XLI to XLVI. Though none of the reactions are essentially new, the experimental skill necessary to manipulate often intractable substances was first-rate. Inversion of configuration at the stage XLII to XLIII was a welcome bonus. 

Bienzymatic Carbonyl Reductase/Nitrilase Catalyzed Route for the Stereospecific Synthesis of P-Hydroxy Acids... 

Scheme 8.3 depicts an efficient and stereospecific synthesis of tadalafil (1) as well as 12a-epf-tadalafil (11). Pictet-Spengler reaction of D-trypto-phan methyl ester hydrochloride 9 with equal molar piperonal by refluxing for 4 h in nitromethane afforded cfs-lO-HCl in 98% ee and 94% yield. The hydrochloride salt of cis tetrahydro-p-carboline derivative a s-10-HCl was directly treated with 1.5 equiv of chloroacetyl chloride in dichloromethane at 0°C in the presence of 3 equiv of triethylamine to form N-chloroacetyl tetrahydro-p-carboline derivative 5 in 92% yield. Then compoimd 5 reacted with 5 equiv of methylamine overnight in DMF at room temperature to furnish tadalafil 1 in 95% yields. 

R J. Reider, P. Davis, P. L. Hughes, and E. J. J. Grabowski, Crystallization-induced asymmetric transformation Stereospecific synthesis of a potent peripheral CCIT antagonist, J. Org. Chem.. 52 955 (1987). 

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