Evolution of Biocatalytic and Chemocatalytic C–H Functionalization Strategy in the Synthesis of Manzacidin C

Because of their unique molecular architecture, the manzacidins have been the subject of intense synthetic efforts in the past two decades. Here, we describe two synthetic approaches toward manzacidin C that center on the enzymatic hydroxylation of unprotected l-leucine. This study also resulted in...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 14; pp. 7407 - 7415
Main Authors Zwick, Christian R, Renata, Hans
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.07.2018
Amer Chemical Soc
Subjects
carbon-hydrogen bond activation
chemical structure
Chemistry
Chemistry, Organic
hydroxylation
leucine
organic chemistry
photocatalysis
Physical Sciences
pyrrolidines
Science & Technology
STEREOINVERSION
NATURAL-PRODUCTS
AMINO-ACIDS
BIOSYNTHESIS
1,3-DIPOLAR CYCLOADDITION
HYDROXYLATION
DIOXYGENASES
BOND FUNCTIONALIZATION
IRON
ALKALOIDS
Online AccessGet full text

Cover

More Information
Summary:Because of their unique molecular architecture, the manzacidins have been the subject of intense synthetic efforts in the past two decades. Here, we describe two synthetic approaches toward manzacidin C that center on the enzymatic hydroxylation of unprotected l-leucine. This study also resulted in the discovery of novel synthetic methodologies, including a photocatalytic C–H azidation of unprotected amino acids. Additionally, we describe the use of hydroxylated l-leucine in the preparation of various densely substituted pyrrolidines.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b00248