Ramage synthesis

Modifying the synthesis of a key tricyclic aldehyde in the Ramage synthesis, subsequent Wittig-Homer reaction successfully linked their synthesis to the target lysergic acid (1). 

Also using the key intennediates in the Ramage synthesis, the newly developed oxidative addition of vinyl triflates to palladium(II) and the Heck reaction paved a way to lysergic acid (1). 

Ramage R, Barron CA, Bielecki S, Holden R, Thomas DW. Solid phase peptide synthesis Fluoride ion release of peptide from the resin. Tetrahedron Lett 1987 28 4105-4108. 

R. Ramage, J. Green, A.J. Blake, An acid labile arginine derivative for peptide synthesis NG-2,2,5,7,8-pentamethylchroman-6-sulphonyl-L-arginine, Tetrahedron 47(1991)6353-6370. 

AR Fletcher, JH Jones, WI Ramage, AV Stachulski. The use of the MJt)-phenacyl group for the protection of the histidine side chain in peptide synthesis. J Chem Soc Perkin Trans 1, 2261, 1979. 

M-L Valero, E.Giralt, D Andreu. Optimized Asp/Glu side chain anchoring in synthesis of head-to-tail cyclic peptides by Boc/OFm/benzyl chemistry on solid phase, in R Ramage, R Epton, eds. Peptides 1996. Proceedings of the 24th European Peptide Symposium, Mayflower, Kingswinford, 1998, pp 857-858. 

R Ramage, I Green. NG-2,2,5,7,8-Pentamethylchroman-6-sulphonyl-L-arginine a new acid labile derivative for peptide synthesis. (Pmc) Tetrahedron Lett 28, 2287, 1987. 

R. Ramage, A. M. MacLeod, and G. W. Rose, Dioxolanes as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-araMiio-2-heptulosonic acid (DAH) and 2-keto-3-deoxy-D-gluconic acid (KDG), Tetrahedron 47 5625 (1991). 

MacDonald AA, Dewitt SH, Ghosh S, Elogan EM, Kieras L, Czarnik AW, Ramage R, The impact of polystyrene resins in solid-phase organic synthesis, Mol. Diversity, 1 183-186, 1996. 

Carpino LA. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupUng additive. J. Am. Chem. Soc. 1993 115 4397-4398. Roberston N, Ramage R. Racemisation studies of a novel coupling reagent for solid phase peptide synthesis. Tetrahedron 1999 55 2713-2720. 

Based upon a consideration of a possible biogenetic pathway to the tricyclo-vetivane group of sesquiterpenoids, MacSweeney and Ramage have accomplished a very elegant synthesis of zizanoic acid (384 = C02H,R = H). The... 

Renaud J, Bischoff SF, Buhl T, Floersheim P, Fournier B, Geiser M, Halleux C, Kallen J, Keller H, Ramage P. Selective estrogen receptor modulators with conformationally restricted side chains Synthesis and structure-activity relationship of ERalpha-selective tetrahydroisoquinoline ligands. J Med Chem 2005 48 364-79. 

Love SG, Muir TW, Ramage R, Shaw KT, Alexeev D, Sawyer L, Kelly SM, Price NC, Arnolds JE, Me MP, and Mayer ly. Synthetic, Structural and Biological Studies of the Ubiquitin System Synthesis and Crystal Structure on an Analogue Containing Unnatural Amino Acids. Biochem J 1997 323 727-734. 

P. M. St. Hilaire, T. Lowary, M. Meldal, K. Bock Synthesis and analysis of glycopeptide libraries and their application in solid phase assays of carbohydrate binding-proteins in Peptides 1996, Proc. Ear. Pept. Symp. (Eds Epton R. Ramage R. Davies J), Mayflower Worldwide, Kingwinford. 1997, pp. 817-818. 

Ramage et al. [89, 90] have reported TFA-labile linkers for the synthesis of peptide amides 37, hydrazides 38 and semicarbazones 39 based on dibenzocyclo-heptadiene scaffold. 

A. MacDonald, R. Ramage, S. H. DeWitt and E. Hogan, Diversomer Technology Recent Advances in the Generation of Chemical Diversity, conference "Combinatorial Synthesis Symposium", Exeter, 1995. 

Another synthesis of quinolizidine is due to the work of Clemo, Ramage, and Raper (133). Ethyl 7-2-pyridylbutyrate (XL) was... 

A.J. Bates, I.J. Galpin, A. Hallett, D. Hudson, G.W. Kenner, G.W. Ramage, R.C. Sheppard, A new reagent for peptide synthesis /z-oxo-bis-[tris-(dimethylamino)phosphonium]-bis-tetrafluoroborate. Helv. Chim. Acta. 58 688-696 (1975)... 

R.B. Woodward, K. Heusler, J. Gosteli, P. Naegeli, W. Oppolzer, R. Ramage, S. Ranaganathan, H. Vorbriiggen, The total synthesis of cephalosporin C., J. Amer. Chem. Soc. 88 852-853 (1966) H. Brockmann, G. Schmidt-Kastner, Valinomycin I. XXVII. Mitt, iiber Antibiotica aus Actinomyceten, Chem. Ber. 88 57-61 (1955)... 

Ramage and coworkers (537) have developed a biomimetic synthesis of pulvinic acids which relies for its success on the facility with which dioxolanones of type (110) undergo nucleophilic attack at the lactone carbonyl group with subsequent extrusion of cyclohexanone. In the synthesis of xerocomic acid (Scheme 15) the dioxolanone (110), obtained as the predominant isomer from reaction between the phos-phorane (109) and methyl (3,4-dibenzyloxyphenyl)glyoxalate, was cleaved with the lithium enolate of /-butyl (4-benzyloxyphenyl)acetate. The intermediate dianion (111) probably exists at first as the chelate (112) which is then broken down on aqueous work up and subsequently cyclised specifically at the less hindered carbonyl group to produce the ester (113). The dianion (111) is analogous to the hypothetical... 

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