TOTAL SYNTHESIS OF (+ -)CAULILIDE(I)

The total synthesis of (+/-) caulilide (1) which shows a potent cytoto xicity is described, Cyclocitral (2) was prepared from citral via citr alylimine in 85%similar to 90% yield, The reaction of 2 with KCN follo wed by dehydration afforded nitrile 3 in 56% yield, Allyl oxidation of 3 was performed by using pyridium dichromate-t-butyl-hydroperoxide to give ketonitrile (4) which was a mixture of geometric isomers of 4a ( cis) and 4b (trans), After separation on a silica gel column, the cis isomer 4a was then hydrolyzed and simultaneously lactonized in cone, H Cl solution to form a Lactone (+/-)-5. The synthesis of caulilide (1) was compl eted by the reduction of 5 with NaBH4. The crude product was separated by high performed chromatography to give the target compoun d (+/-)-1.