1-.beta.7,8-trihydroxy vitamin D.sub.2, 1.beta.7,8-trihydroxy vi

Details 1-.beta.7,8-trihydroxy vitamin D.sub.2, 1.beta.7,8-trihydroxy vi 1-.beta.7,8-trihydroxy vitamin D.sub.2, 1.beta.7,8-trihydroxy vi

1993-08-11

1995-08-29

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549336, 552653, C07D31720, C07C40100

Patent

active

054461740

ABSTRACT:
There are disclosed novel compounds that can be used to derive therefrom a fragment that corresponds to an A-ring which is to he combined with fragments which respectively correspond to C- and D-rings in synthetic formation of vitamin D.sub.3 derivatives by cleaving the 7,8-bondings by means of oxidizing agents following any known process. According to the invention, there is provided an industrially efficient and effective method of manufacturing above compounds that utilizes allylic hydroxylation to add an oxygen function group to position C(1), a method which is completely different from any existing synthetic methods.

REFERENCES:
patent: 4755329 (1988-07-01), DeLuca et al.
D. Desmaele et al., "Synthesis of A-ring of 1S-hydroxykohlcalciferol", Tetrahedron Letters, vol. 26, No. 44, pp. 4941-4944 (1985).
J. Miguel Aurrecoechea et al., "A Short, Enantiospecific Synthesis of the 1.alpha.-Hydroxyvitamin D Enyne A-Ring Synthon," Tetrahedron Letters, vol. 28, No. 42, pp. 4947-4950 (1987).
Hector F. DeLuca et al., "Vitamin D: Recent Advances", Ann. Rev. Biochem., 52: 411-419 (1983).
Roselyne Pardo et al., "Synthese des metabolites de la vitamine D", Bulletin De La Societe Chimque De France, No. 1, pp. 11-98 -11-114 (1985).
Nubuo Ikegawa et al., "Synthesis of Active Forms of Vitamin D(I)-Recent Advances," Organic Synthetic Chem., 37: pp. 755-770 (1979).
Martin J. Calverley, "Synthesis of MC 903, A Biologically Active Vitamin D Metabolite Analogue," Tetrahedron Lts. vol. 43, No. 20, pp. 4609-4619 (1987).
B. Lythgoe, "Synthetic Approaches to Vitamin D and its Relatives," Chem. Soc. Rev., 9, pp. 449-475 (1980).

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