Coleman synthesis

The Coleman synthesis commenced with a [4+2] cyclization to achieve naphthalene 30 (Scheme 7.4). This convergent process required four steps to obtain diene 27 and five steps to attain dieneophile 28. Three further functional group transformations were required to complete aldehyde 31. This novel process realized the installation of all the carbon and oxygen substituents in a regioselective manner. 

In the first year of the 20th century, there was a new finding concerning the synthesis of pteridine, known as Gabriel-Coleman synthesis. In this method, pteridine derivatives are generally produced through the condensation of 2,3-diaminopyrimidine 55 with a-diketone (Eq. 5). One century has passed since the development of Gabriel-Coleman synthesis, however, modern synthetic procedures of tetrahydrobiopterin (43) conceptually depend on this synthe-... 

The application of Gabriel-Coleman synthesis to the synthesis of biopterin (30) is reliable, however, it has a serious problem in that the condensation of the pyrimidine precursor with asymmetrically substituted sugar derivatives is sometimes less regioselective or even nonregioselective. For example,... 

Cyclopentadiene, b.p. 40°, is obtained by heating commercial 85% dicyclopentadiene (e.g., from Matheson, Coleman and Bell Company, Norwood, Ohio) under a short column (M in. diameter X 8-12 in. length) filled with glass helices. The distilled cyclopentadiene is collected in a receiver which is maintained at Dry Ice temperature until the cyclopentadiene is used. Methylcyclopentadiene and other substituted cyclopentadienes such as indene may also be employed for the synthesis of the correspondingly substituted ferrocenes. In these cases, the reaction of the hydrocarbon with sodium is much slower than with cyclopentadiene, and refluxing for several hours is required to complete the reaction. 

Azinomycins A and B (64 and 65 Scheme 11.5) [115, 116] were isolated in 1986 from Streptomyces griseofuscus at the SS pharmaceutical company in Japan and were found to have potent in vitro cytotoxicities [117] and to display significant in vivo antitumor activity [118]. Since their discovery [117] and structure determination [119], their unusual molecular framework has attracted the attention of many chemists interested in their mode of action and in developing synthetic approaches to them [115,116]. The first total synthesis of azinomycin A was achieved in 2000 by Coleman et al. [120]. 

Palchetti I, Mascini M (2005) Electrochemical Adsorption Technique for Immobilization of Single-Stranded Oligonucleotides onto Carbon Screen-Printed Electrodes. 261 27-43 Pascal R, Boiteau L, Commeyras A (2005) From the Prebiotic Synthesis of a-Amino Acids Towards a Primitive Translation Apparatus for the Synthesis of Peptides. 259 69-122 Paulo A, see Santos I (2005) 252 45-84 Perez EM, see Leigh DA (2006) 265 185-208 Perret F, see Coleman AW (2007) 277 31-88 Perron H, see Coleman AW (2007) 277 31-88 Pianowski Z, see Winssinger N (2007) 278 311-342 Piestert F, see Gansauer A (2007) 279 25-52... 

During the same year as Hauser s reported synthesis of calphostin D, the Coleman laboratories published an alternative approach to this family of natural products [32]. This report included the enantioselective syntheses of both phleichrome and calphostin A and, like the previous approaches, started from an enantioenriched naphthalene. 

C.R. Herron, K.S. Coleman, R.S. Edwards, B.G. Mendis, Simple and scalable route for the bottom-up synthesis of few-layer graphene platelets and thin films, Journal of Materials Chemistry, 21 (2011) 3378. 

Coleman DR, Royer GP. New hydrogenation catalyst-palladium poly(ethyleneimine) ghosts—applications in peptide synthesis. J Org Chem 1980 45 2268-2269. 

T.R. DeGrado, R.E. Coleman, S. Wang, S.W. Baldwin, M.D. Orr, C.N. Robertson, T.J. Polascik, D.T. Price, Synthesis and evaluation of F-labeled choline as an oncologic tracer for positron emission tomography Initial findings in prostate cancer. Cancer Res. 61 (2001) 110-117. 

G. A. Brine, K.G, Boldt, M.L. Coleman, E.E. Williams, T.M. Krcelic u. F.I. Carroll, Phencyclidine Relat. Arylcyclohexylamines Present Future Appl., Proc. Jt. Fr.-US Semin. Chem. Pharmacol., Present Future Ther. Appl. Drug Abuse Aspects Arylcyclohexylamines, NPP Books, Ann Arbour, Mich., 1983 , .Synthesis and Carbon-13-Nuclear Magnetic Resonance Analysis of Arylcyclohexylamines Related to Phe-nylcyclidine". 

Coleman, M.J., Goodyear, M.D., Lathan, D.W.S., Whitehead, A.J. A convenient method for the N-acylation and esterification of hindered amino acids synthesis of ultra short acting opioid agonist, remifentanil, Synlett1999, 1923-1924. 

Coleman, T.M. and Huang, F. (2002) RNA-catalyzed thioester synthesis, Chem. Biol. 9, 1227-1236. 

Coleman RS, Lu X (2006) Total Synthesis of Strobilurin B Using a Hetero-bw-Metallated Pentadiene Linchpin. Chem Commun 423... 

Dr. Bill Coleman, for several chemical steps in Syntex s synthesis of the oral contraceptive chlormadinone. With Haldor Christensen, sodium dispersion chemistry led to a superior process for the manufacture of the Eh Lilly herbicide, diphenamid. We devised novel patented chemistry, with the inspiration of Dr. Martin Hultquist, for the manufacture of DDQ. The list could go on and on, but the essence is that in Arapahoe we became chemical process development chemists. We learned that there were no such chemists as steroid chemists, organometallic chemists, heterocyclic chemists, and so on. There are only process development chemists, capable of synthesizing anything. Being scientists in a small company we also learned to accommodate other disciplines and business requirements in creating our chemical processes. 

Mendlik, M.T., Tao, P., Hadad, C.M., Coleman, R.S., and Lowary, T.L. (2006) Synthesis of L-daunosamine and L-ristosamine glycosides via photo-induced aziridination. Conversion to thioglycosides for use in glycosylation reactions. Journal of Organic Chemistry, 71 (21), 8059-8070. 

Enzymes and regulation of TAG synthesis have been reviewed in depth by Coleman et al. (2000, 2004). 

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