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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.
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KCS