Method of obtaining derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi

Details Method of obtaining derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi Method of obtaining derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi

1985-11-27

1987-11-17

Jiles, Henry R.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549414, 549415, 549465, C07D307935

Patent

active

047075546

ABSTRACT:
A new method has been disclosed for obtaining derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi.,5.dbd.-dihydroxy-3,3a.beta.,4,5,6,6a.beta.- hexahydro-2H-cyclopenta [b] furane useful in the synthesis of prostaglandins or their analogs, and a method for obtaining new sulphonyl initial compounds of the general formula 4, in which Z denotes a hydrogen atom or a protective group, Y denotes a group of the formula .dbd.CHOZ.sup.1, in which Z.sup.1 has the meaning stated for Z, whereby protective groups Z and Z.sup.1 may be the same or different, and Ar denotes optionally a substituted aryl group.
In the method according to the invention the new sulphonyl derivative of the general formula 4 is alkylated with an electrophilic agent comprising: carbonyl derivatives, oxiranes and halohydrins or their derivatives; the alkylation product is transformed into derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi.,5.alpha.-dihydroxy-3,3a.beta.,4,5,6,6a.beta .-hexahydro-2H-cyclopenta[b] furane in reactions which ensure obtaining a double bond C.sub.13 -C.sub.14.
New sulphonyl initial compounds of the general formula 4 are obtained from lactone of the general formula 11, in which Z has the above stated meaning and L.degree. denotes a leaving group, which is transformed into a sulphide; the obtained lactone-sulphide is reduced to lactol, and thereafter lactol-sulphide is oxidized to the sulphonyl derivative.

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