Current Trends in Organic Synthesis by Steven D. Bull, Stephen G. Davies, David J. Fox (auth.),
By Steven D. Bull, Stephen G. Davies, David J. Fox (auth.), Carlo Scolastico, Francecso Nicotra (eds.)
The final twenty years have obvious a swift development within the man made processing of either easy and complicated molecules, aimed toward assembly the wishes of society in all elements of existence. Many efforts were dedicated to the advance of latest biologically energetic compounds, new fabrics with leading edge houses reminiscent of bio-compatibility, new catalysts that let hugely selective ameliorations, and applied sciences that facilitate the bogus professional cesses. This booklet is a compendium of modern growth in some of these elements of man-made chemistry. It collects the lectures of the XII foreign convention on natural Synthesis, held in Venice from June 28 to July 2, 1998, during which the current nation of paintings of this self-discipline has been said. the subjects coated comprise: combinatorial chemistry, new artificial tools, stereo selective synthesis, metal-mediated synthesis, and goal orientated synthesis. The booklet collects the contributions, within the pointed out themes, of forty three scientists from 19 diversified international locations. The contributions provided within the convention as plenary lectures are pronounced within the first component to the booklet. specific realization has been devoted to combinatorial chemistry, a brand new and promising technique for the synthesis of libraries of pharmaco logically fascinating compounds in an effort to permit the automated pharmacological screening of millions of compounds. The convention has devoted to combinatorial chemistry a mini-symposium during which scientists from academy and firms have defined the present tendencies of this very new technology.
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37 36 1. KHMDS, 18-cr-6 02, THF; 2. Bz 20. DMAP CH2CI2 (50%) "15 (~Pr)2NEt (61%) OBOM PMBMO CH3 CH o 3 OBz 38 DDQ CH2CI2, H20 (68%) 39 CH3 OMOM OBOM H3C AI(Ot-Bu)~ C 6H6 ,l> (77%) ~ o OH CH3 CH3 OBz OBz 40 41 Scheme 8 The task of devising the proper C-ring synthon now had to be addressed. The enantiomerically pure (Z)-vinyl iodide 42, conveniently available from D-ribose functioned 30 admirably well up to the point of aldol cyclization (Scheme 9). The aldehyde obtained from 43 enters into ring closure, but only after ~-elimination (see 44) and recapture of methano1.
Am. Chem. Soc. 117, 653 (1995). 7. S. 1. Danishefsky, 1. 1. Masters, W. B. Young, 1. T. Link, L. B. Snyder, T. V. Magee, D. K. lung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, and M. 1. DiGrandi J. Am. Chem. Soc. 118, 2843 (1996). 8. P. A. Wender, N. F. Badham, S. P. Conway, P. E. Fioreancig, T. E. Glass, C. Granicher, 1. B. Houze, 1. lanichen, D. Lee, D. G. Marquess, P. L. McGrane, W. Meng, T. O. Mucciaro, M. Mlihlebach, M. G. Natchus, H. Paulsen, D. B. Rawlins, 1. Satkofsky, A.
MOMCI . (i-Pr)2NEt 3 H~C CH 3 H~C CH H~C CH 3 OMOM OMOM H 3. MOMCI, (i-Pr)2NEt (96%) OMOM ~ 0 H H PMPO hi 0 PMPO 32 31 0 ~ 33 Scheme 6 This array of functionality proved to be most accommodating and especially conducive to our goals. Thus, the steric bulk of the OMOM group further enhanced endo addition to the adjacent carbonyl. Also, its inductive effect sufficiently reduced the acidity of the a-carbonyl proton that direct condensation with alkcnyllithium reagents was now possible. In addition, the subsequent charge-accelerated sigmatropic rearrangement of the resulting exo carbinols 29 delivered tricyclic products that feature the characteristic B-ring oxygenation pattern resident in 2 (Scheme 7).