Preparation of (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl meth

Details Preparation of (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl meth Preparation of (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl meth

1995-03-03

2000-08-29

Shaver, Paul F.

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

Organic compounds

Silicon containing

556437, 556482, 549215, 549546, 568361, 568377, 568667, 568823, 568825, C07F 708

Patent

active

061111252

ABSTRACT:
A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia ##STR1## which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the general formula II ##STR2## where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI ##STR3## by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII ##STR4## with Lewis acids and, where appropriate, removal of the protective group. Also claimed are the novel intermediates of the formula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.

REFERENCES:
patent: 5155243 (1992-10-01), Fujiwa et al.
patent: 5382676 (1995-01-01), Kuwana et al.
patent: 5424460 (1995-06-01), Duhamel et al.
patent: 5565489 (1996-10-01), Kaneko et al.
patent: 5801123 (1998-09-01), Sakai et al.
J. Chem. Soc. 1961, 00 4019 f.
Helv. Chim. Acta 66, 7 (1983) No. 192, pp 1939-60
J. Mol Struct. 226 (1992) pp 91-92.
Quim Nova 14 (1991) pp 22-25.
Carrotinoid Chem. Biochem. Proc. Int. Symp. Carotenoids, 6th Meeting, Date 1981, pp. 71-86, edited by Britten G. Goodween T.W., Pergamon, Oxford.

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