Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy

Details Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy

1992-03-12

1993-12-28

Tsang, Cecilia

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

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 77, 554113, 549292, C09F 700, C07D30930

Patent

active

052741435

ABSTRACT:
A process for the preparation of a tautomeric mixture of compounds of the formulas ##STR1## wherein W is hydrogen or C.sub.6 H.sub.13, which comprises treating a compound of the formula ##STR2## wherein R is unsubstituted or substituted alkoxy, arylalkoxy, aryloxy or amine and R.sup.1 is hydrogen or when R is alkoxy, substituted alkoxy, substituted amine, unsubstituted or substituted arylalkoxy R.sup.1 can also be metal, with a compound of the formula ##STR3## wherein W is as described above, both X and Y are reducible groups or X is hydrogen and Y is a reducible group or Y is hydrogen and X is a reducible group and, Z is hydroxy or a leaving group to form the compound of formula IV ##STR4## wherein W, X, Y and R are as defined above, the compound of formula IV is treated with a low valent metal to form a tautomeric mixture of compounds of formulas I and Ia, which are useful in the synthesis of tetrahydrolipstatin.

REFERENCES:
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Barbier, et al., Synthesis of Tetrahydrolipstatin and Tetrahydroesterastin, Compounds with a .beta.-Lactone Moiety. Stereoselective Hydrogenation of a .beta.-Keto & Lactone and Conversion of the .delta.-Lactone into a .beta.-Lactone, J. Org. Chem., vol. 53, pp. 1218-1221 (1988).
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