| The formal enantioselective total synthesis of the polyketide marine natural product (-)-clavosolide A is presented. The construction of the beta- C-glycoside subunit is highlighted by a one-pot oxocarbenium cation formation/reduction sequence. Double Yamaguchi macrolactonization and subsequent deprotection will afford the diolide aglycon in 17 steps (longest linear sequence) from commercially available crotonaldehyde. Our plan develops methods and synthetic strategies that allow the expeditious and stereoselective construction of this densely oxygenated 16-membered diolide. The synthetic study of this marine natural product, synthetic strategies, methodology, and results is reported herein. |
