Late‐Stage β‐Epimerization. A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)‐Murolic Acid | Zendy

Fernandes Rodney A. | Zendy; Patil Pradnya H. | Zendy; Chowdhury Asim K. | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research