Total Synthesis and Structure Confirmation of Cryptocaryol A

  Total Synthesis and Structure Confirmation of Cryptocaryol A European journal of chemistryEarly View (Online Version of Record published before inclusion in an issue)
D. Srinivas Reddy and Debendra K. Mohapatra
Article first published online: 19 DEC 2012 | DOI: 10.1002/ejoc.201201309

Thumbnail image of graphical abstract

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.

Linkshttp://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201309/abstract

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.

Dedicated to Dr. Mukund K. Gurjar on the occasion of his 60th birthday

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