Clardy synthesis

Uses of FeCl3/Ac20 methodology in synthesis include the taxusin synthesis of Holton et al. (Sch. 2) [15], the Forsyth and Clardy synthesis of (+)-didemnenones A and B [16], and the synthesis of a nodulation factor (NodRf-III) by Fraser-Reid and coworkers [17]. 

The intramolecular [2 + 2] photocycloaddition of an a-carboxy enamide with an olefin has been elegantly exploited independently by Pirrung and by Clardy and coworkers in the synthesis of the toxic amino acid 2,4-methanoproline via irradiation of 32 (equation 9)15. 

For the synthesis of cyclobutane-containing amino acids using a similar photochemical approach see P. Hughes and J. C. Clardy 7. Org. Chem., 1988, 53, 4793. 

Hughes and Clardy described the first synthesis of 8 in 1989. This important work contains no indication of the chemical properties of the new amino acid, except for a passing comment regarding its instability. It seemed to us that some knowledge of the chemistry of 8 was essential to the success of the luzopeptin effort. In that context, the issue of... 

DANISHEFSKY, S., M. HIRAMA, N. FRITSCH, J. CLARDY. 1979. Synthesis of disodium prephenate and disodium epiprephenate. Stereochemistry of prephenic acid and an observation on the base-catalyzed rearrangements of prephenic acid to p-hydroxyphenyllactic acid. J. Am. Chem. Soc. 101 7013-7018. 

Martyn, D.C., Beletsky, G., Cortese, J.F., Tyndall, E., Liu, H., Fitzgerald, M.M., O Shea, T.J., Liang, B., and Clardy, J. (2009) Synthesis and in vitro DMPK profiling of a 1,2-dioxolane-based library with activity against Plasmodium falciparum. Bioorganic and Medicinal Chemistry Letters, 19, 5657-5660. 

Holbert G W, Ganem B, Van Engen D, Clardy J, Borsub L, Chantrapromma K, Sadavongvivad C, Thebtaranonth Y 1979 Shikimate-derived metabolites. Revised structure and total synthesis of pipoxide. Tetrahedron Lett 715-718... 

Martin, M., and J. Clardy The Synthesis of Pacifigorgiol. Pure Appl. Chem. 54, 1915 (1982). 

Evans DA, Kaldor SW, Jones TK, Clardy J, Stout TJ. Total synthesis of the macrolide antibiotic cytovaricin. J. Am. Chem. Soc. 1990 112(19) 7001-7031. 

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