KCS

In the course of our research program aimed at finding new synthetic methods in the stereoselective construction of pyran rings via stepwise allylic transfer reactions, we became quite interested in designing a sequential allylic transfer reaction from allenylstannane with two aldehydes to form acyclic 1,3-diol possessing versatile functional groups as shown in Scheme We describe herein ourdiscovery of a sequential reaction for the synthesis of 2-(1-stannylvinyl)-1,3-diols with the generation of threecontiguous stereogenic centers in exceptional stereoselectivity, and its application to the synthesis of ()-avenaciolide in three steps.