Synthesis of 9-substituted carbacyclin analogs

…, PD Johnson, AW Harrison

Index: Aristoff, Paul A.; Johnson, Paul D.; Harrison, Allen W. Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5341 - 5348

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Citation Number: 30

Abstract

The synthesis of a series of 9-substituted carbacyclin analogues with potent platelet antiaggregatory activity is described. The key step for the formation of 9-acetylene compounds (eg, 8d) utilized a modification of the Schwartz procedure involving the nickel- catalyzed conjugate addition of the appropriate alkynyl aluminate to bicyclo [3.3. 0] oct-l-en- 3-one (2). It was found that 9-methylcarbacyclin (8b) could be prepared by a simii ...

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