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Topic Name: Total synthesis and study of 6-deoxyerythronolide B by late-stage C–H oxidation
Category: Chemical
Research persons: Erik M. Stang ,M. Christina White
Location: Illinois, United States
Details
Among the frontier challenges in chemistry in the twenty-first century are
the interconnected goals of increasing synthetic efficiency and diversity in the
construction of complex molecules.
Oxidation reactions of C–H bonds, particularly when applied at late stages of
complex molecule syntheses, hold special promise for achieving both these goals.
Here researchers report a late-stage C–H oxidation strategy in the total
synthesis of 6-deoxyerythronolide B (6-dEB), the aglycone precursor to the
erythromycin antibiotics.
An advanced intermediate is cyclized to give the 14-membered macrocyclic core
of 6-dEB using a late-stage (step 19 of 22) C–H oxidative macrolactonization
reaction that proceeds with high regio-, chemo- and diastereoselectivity
(>40:1).
A chelate-controlled model for macrolactonization predicted the
stereochemical outcome of C–O bond formation and guided the discovery of
conditions for synthesizing the first diastereomeric 13-epi-6-dEB precursor.
Overall, this C–H oxidation strategy affords a highly efficient and
stereochemically versatile synthesis of the erythromycin core.
About the researchers :
Erik M. Stang
& M. Christina White
Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801,
USA
Correspondence to: M. Christina White e-mail: white@scs.uiuc.edu
| Tags: |
complex molecules - Total synthesis - 6-deoxyerythronolide B - late-stage C–H oxidation - |
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