4-trisubstituted silyl protected hydroxy-6-oxo-tetrahydropyran-2

Details 4-trisubstituted silyl protected hydroxy-6-oxo-tetrahydropyran-2 4-trisubstituted silyl protected hydroxy-6-oxo-tetrahydropyran-2

1983-12-21

1986-11-25

Naff, David M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549292, 548494, C07D30930

Patent

active

046250395

ABSTRACT:
6-trans-indol-2-yl-ethenyl)-4-hydroxy-tetrahydro-2H-pyran-2-ones of formula I are obtained by a multi-step reaction involving the procedure: ##STR1## wherein p.sup.1 is trisubstituted silyl protective group, and Z is a 2-indolyl radical which may be bear at the 4, 5, 6 and 7-positions up to two substituents such as alkyl, alkoxy, halo and CF.sub.3, and at either one the 1 or 3-positions a substituted or unsubstituted phenyl; and at the other an assymetric alkyl, cycloalkyl or aralkyl radical. Compounds I, e.g. (E)-trans-6-[1'-methyl-3'-(4"-fluorophenyl)indol-2'-ylethenyl]3,4,5,6 -tetrahydro-4-hydroxy-2H-pyran-2-one(4R,6S); are useful as anti-atheroselerotic agents.

REFERENCES:
patent: 4474971 (1984-10-01), Wareing
Katoitzky, "Advances in Heterocyclic Chemistry", vol. 2, p. 301, Academic Press, 1963.
House, "Modern Synthetic Reactions", 2nd ed., pp. 692-693.
Morrison, "Organic Chemistry", 3rd ed., pp. 218-219.

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