Premium
Total Synthesis and Structure Confirmation of Cryptocaryol A
Author(s) -
Reddy D. Srinivas,
Mohapatra Debendra K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201309
Subject(s) - chemistry , total synthesis , enantioselective synthesis , polyol , ring closing metathesis , metabolite , stereochemistry , metathesis , combinatorial chemistry , organic chemistry , catalysis , biochemistry , polymer , polyurethane , polymerization
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.