Syntheiss of (-)-chanoclavine I

Article abstract of DOI:10.1016/0957-4166(94)80122-3

The total enantioselective synthesis of (-)-chanoclavine I 2 in twelve steps from indole-4-carboxaldehyde 4 is described. The key-step 3 → 6 which involves the formation of the C ring by creation of the C5-C10 bond is catalyzed by a chiral palladium (0) complex. The chiral ergoline synthon 6 is produced with an excellent diastereo- and enantioselectivity (up to 95% ee).