DYKAT of Baylis-Hillman adducts: concise total synthesis of furaquinocin E.
Baylis-Hillman adducts are easily accessible building blocks; the lack of asymmetric versions of the Baylis-Hillman reaction has however precluded their widespread use in asymmetric synthesis. A Pd-catalyzed DYKAT on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck reaction, allows the enantio- and diastereoselective construction of dihydrobenzofurans in a very efficient manner. These synthons represent the core structure of the furaquinocins. Introduction of different side chains and use of different squaric acid derivatives for the construction of the naphthoquinone allow the flexible synthesis of this class of natural products. This new approach is successfully applied to the synthesis of furaquinocin E and an analogue.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Thiel
Oliver R
OR
Tsui
Hon-Chung
HC
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007700:Kinetics; D009285:Naphthoquinones / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D009285:Naphthoquinones; C068889:furaquinocin E