Fukuyama

Six protective groups for alcohols, which may be removed successively and selectively, have been listed by E.J. Corey (1972B). A hypothetical hexahydroxy compound with hydroxy groups 1 to 6 protected as (1) acetate, (2) 2,2,2-trichloroethyl carbonate, (3) benzyl ether, (4) dimethyl-t-butylsilyl ether, (5) 2-tetrahydropyranyl ether, and (6) methyl ether may be unmasked in that order by the reagents (1) KjCO, or NH, in CHjOH, (2) Zn in CHjOH or AcOH, (3) over Pd, (4) F", (5) wet acetic acid, and (6) BBrj. The groups may also be exposed to the same reagents in the order A 5, 2, 1, 3, 6. The (4-methoxyphenyl)methyl group (=MPM = p-methoxybenzyl, PMB) can be oxidized to a benzaldehyde derivative and thereby be removed at room temperature under neutral conditions (Y- Oikawa, 1982 R. Johansson, 1984 T. Fukuyama, 1985). 

A number of people must be thanked for their contributions and help in completing this project. I am grateful to Gordon Bundy, who loaned me this card file, which provided many references that the computer failed to find, and to Bob Williams, Spencer Knapp, and Tohm Fukuyama for many references on amine and amide protection. I thank Theo Greene who checked and rechecked the manuscript for spelling and consistency and for the herculean task of checking all the references to make sure my 3s and 8s and 7s and 9s were not interchanged, all w iihout... 

SOURCE Transport and Structural Formation in Plasmas by K. Iloh, S.-I. Itoh, and A. Fukuyama, Institute of Physics Publishing Ltd., 1999. p. 24. 

In a versatile stereocontrolled total synthesis of (+)-vinblastine, Fukuyama used a base-promoted macrocyclization of the N-nosylate and the terminal epoxide moiety present in 88 as one of the key steps, giving the 11-membered-ring product 89 in 82% yield (Scheme 8.23) [42],... 

Like the mitomycins, FR900482 (6), FR66979 (7), FK973 (8), and FK317 (9) have also been shown to crosslink DNA both in vivo [68-70], and in vitro after reductive activation [71-76] with selectivity for the 5 -CpG-3 sequence [77]. The mechanism outlined in Figure 11.2 was originally proposed by Goto and Fukuyama [78] and has been verified by the experimental work of Williams and Hopkins [71-77, 79]. Reduction of the N-O bond produces intermediate 27, which can lose a molecule of water to form 28, which reacts with DNA by a mechanism similar to that found... 

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