Palladium Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles. 3. Total Synthesis of (+/-)-Aurantioclavine

Article abstract of DOI:10.1021/jo00391a027

(+/-)-Aurantioclavine (9) was synthesized in overall 23percent yield and 13 steps from comercially available starting materials.The synthesis involved palladium(II)-catalyzed indole ring formation, nickel(0)/zirconium(IV)-assisted introduction of one side chain, palladium(0)-catalyzed introduction of the other side chain, acid-catalyzed cyclization to form the seven-membered ring, and photolytic reductive detosylation to produce 9.