Total Synthesis and Structure Confirmation of Cryptocaryol A1. Issue 6 (19th December 2012)

• Record Type: Journal Article
• Authors: Reddy, D. Srinivas; Mohapatra, Debendra K.
• Is Part Of: European journal of organic chemistry. Issue 6(2013)
• Page Start: 1051
• Page End: 1057
• Publication Date: 2012-12-19
• Subjects: Natural products -- Asymmetric synthesis -- Synthetic methods -- Protecting groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201309
• Languages: English
• ISSNs: 1434-193X

Abstract

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. 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.