Total synthesis and structure confirmation of cryptocaryol A

Article abstract of DOI:10.1002/ejoc.201201309

The first enantioselective total synthesis of Pdcd4-stabilizing cryptocaryol A, a secondary metabolite obtained from a tropical tree, has been achieved through an iterative approach to the 1,3-polyol motif. The key steps are a Maruoka allylation, a Reetz chelation-controlled allylation with 1,3-induction, iterative diastereoselective iodocyclization, and ring-closing metathesis reactions. Maruoka asymmetric allylation, chelation-controlled 1,3-induced allylation, iterative iodocyclization and ring-closing metathesis reactions were used sequentially to achieve the first total synthesis and structure confirmation of cryptocaryol A. Copyright