Total syntheses of the diterpenoids (-)-kolavenol and ( -)-agelasine B

Article abstract of DOI:10.1016/S0040-4039(00)60896-1

The trans-clerodane diterpenoids (-)-kolavenol (2) and (-)-agelasine B (1) have been prepared from the enantiomerically pure decalone 3. The key steps of the syntheses involve the stereo selective alkylation of the nitrile 4 (to give 5), the efficient coupling of the iodides 10 and 11 to produce the clerodane skeleton 12, and the electrochemical reduction of 16 to provide (-)-1.