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Late‐Stage β‐Epimerization. A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)‐Murolic Acid
Author(s) -
Fernandes Rodney A.,
Patil Pradnya H.,
Chowdhury Asim K.
Publication year - 2014
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.201301287
Subject(s) - chemistry , epimer , orthoester , dihydroxylation , total synthesis , yield (engineering) , reagent , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
The first total synthesis of (+)‐murolic acid is accomplished in 17 steps from ester 9 in 14.8 % overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson–Claisen rearrangement and α‐methylenation using Stiles reagent. A beneficial late stage β‐epimerization reverted a stereodivergent relay to a stereoconvergent completion of an efficient synthesis of (+)‐murolic acid.