Optically active carbacyclin intermediates and processes for the

Details Optically active carbacyclin intermediates and processes for the Optically active carbacyclin intermediates and processes for the

1986-05-30

1989-03-21

Rollins, John W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549332, C07D31772

Patent

active

048144681

ABSTRACT:
New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octane-3-on e, by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.

REFERENCES:
Kojima et al., "Total Synthesis of 9(O)-Methanoprostacyclin and its Isomers" in Tet. Lett., 39, pp. 3743-3746, (1978).
Shibasaki et al., "New Synthetic Routes to 9(O)-Methanoprostacyclin, A Highly Stable and Biologically Potent Analog of Prostacyclin" in Tet. Lett., 5, pp. 433-436, (1979).
Sankyo Co., Ltd., "Optical Resolution of Methanocyclin Intermediates" in Chemical Abstracts, 101, 191879e, (1984).
Hiroi et al., "Synthetic Studies on Iridoid Terpenes via Regioselective Sulfenylation of .beta.-Ketoesters and Oxidative Cleavage of .beta.-Thioalcohols--A Novel Synthetic Route to (.+-.)-Loganin-" in Chemistry Letters, 4, pp. 559-562, (1981).

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