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

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549336, 556445, 556446, 556449, 560256, 568819, C07D31720, C07C 3521

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active

052833453

ABSTRACT:
There are disclosed novel compounds that can be used to derive therefrom a fragment that corresponds to an A-ring which is to be comined 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 chemical reaction of allylic acid 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.
Desmaele et al., "Synthesis of A-ring of 1S-hydroxykohlcalciferol", Tetrahydron Letters, 26:4941 (1985).
Okamura et al., "A Short, Enantiospecific Synthesis of the 1.alpha.-Hydroxyvitamin D Enyne A-Ring Synthon", Tetrahydron Letters, 28(42):4947-4950 (1987).
DeLuca et al., "Vitamin D: Recent Advances", Ann. Rev. Biochem., 52:411-419 (1983).
Ikegawa et al., "Synthesis of Active Forms of Vitamin D(I)--Recent Advances", Organic Synthetic Chem., 37:755 (1979).
Calverley, "Synthesis of MC 903, A Biologically Active Vitamin D Metabolite Analogue", Tetrahydron, 43(20):4609-4619 (1987).
Lythgoe "Synthetic Approaches to Vitamin D and its Relatives", Chem. Soc. Rev., 9:449 (1980).

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