MacDonald synthesis

Clezy s modification of the MacDonald synthesis using a 5,5 -diformyl-pyrro-ketone instead of a diformyl-pyrromethane has been extended to the synthesis of the a-oxy-derivative of mesoporphyrin IX and to the y-oxy-derivative of protoporphyrin IX (Scheme 3). The iron complex of the latter undergoes oxidative ring opening in pyridine solution to form biliverdin IX-y (25), the parent compound of a series of three green pigments found in certain types of butterflies and caterpillars this provides a model for their probable mode of biosynthesis. 

R. Bissessur and J. MacDonald, Synthesis and characterization of halo-substituted polyani-linesA OP04 nanocomposites. Mater. Chem. Phys., 106, 256-259 (2007). 

R. N. MacDonald, Macromolecular Synthesis, Vol. 3, John Wiley Sons, Inc., New York, 1968. 

MACDONALD Porptiynn Synthesis Poiphyrme synthesis from dipynolemethanes... 

At about the same time that MacDonald and Fletcher worked on their synthesis of 2-deoxy ribose 5-phosphate, we ourselves tried to work out a synthesis for the same compound, using a quite different approach. 

Scheme 9. Macdonald and Dolan synthesis of tropinone (124). Reagents i, LDA, CTMS, Et3N, DMF ii, DME, CCl3COONa, A iii, HQ iv, MeOH, 0°C, MeNH2 v, (n-C H9)3SnH.

G. Macdonald, L. Alcaraz, N. J. Lewis, R. J. K. Taylor, Asymmetric Synthesis of the mC7N Core of the Manu-mycin Family Preparation of (+)-MT 35214 and a Formal Total Synthesis of (-)-Alsamyciri , Tetrahedron Lett. 1998, 39, 5433-5436 and references therein. 

The MacDonald-Fischer degradation 4 has been used in the synthesis of 5-deoxy-L-arabinose222 from L-rhamnose, and it could be adapted to the preparation of other deoxy sugars. 

Bravo, R and MacDonald-Bravo, H. (1987) Changes in the nuclear distribution of cyclin (PCNA) but not its synthesis depend on DNA replication EMBO J 4, 655-661... 

Taylor RJK, Alcaraz L, Kapfer-Eyer I, Macdonald G, Wei X, Lewis N (1998) Synthesis 775... 

Scheme 3 "2+2" Condensation of dipyrromethanes by the MacDonald method and "3+1" synthesis of etioporphyrins.

Other quercitols have been synthesized by catalytic hydrogenolysis of the corresponding inososes (see p. 180). All the known quercitols are shown, with their names, in formulas CXXXIX-CXLIV according to Angyal and Macdonald s proposals,6 the quercitol of acorn is called (+)-profo-quercitol, and natural viburnitol is named (—)-w 6o-quercitol the corresponding Fletcher-Anderson-Lardy names are (+)-1 -deoxy-mwco-inositol and ( —)-1-deoxy-WM/o-inositol. Synthesis of the four as-yet-unknown diastereomers should not present serious difficulties. 

Hasmall SC, James NH, Macdonald N, et al. 2000. Species differences in response to diethylhexylphthalate suppression of apoptosis, induction of DNA synthesis and peroxisome proliferator activated receptor alpha-mediated gene expression. Arch Toxicol 74 85-91. 

In the case of allocolchicinoids, a non-phenolic intramolecular oxidative coupling was used by Macdonald for the total synthesis of ( )-iV-acetylcolchinol 31, Fig. (12) [96]. 

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. 

Figure 33.9. The two-cell-two-gonadotropin model of estradiol synthesis in ovarian follicles. (Adapted from and reproduced with permission from Carr, B. R., MacDonald, P. C., and Simpson, E. R. The role of lipoproteins in the regulation of progesterone secretion by the human corpus luteum. Fertil. Steril. 38, 303-311, 1982.)...

---