Total syntheses of vancomycin and eremomycin aglycons

David A. Evans; Michael R. Wood; B. Wesley Trotter; Timothy I. Richardson; James C. Barrow; Jeffrey L. Katz

doi:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Total syntheses of vancomycin and eremomycin aglycons

David A. Evans, Michael R. Wood, B. Wesley Trotter, Timothy I. Richardson, James C. Barrow, Jeffrey L. Katz

Research output: Contribution to journal › Article › peer-review

259 Scopus citations

Abstract

Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin-resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations.

Original language	English (US)
Pages (from-to)	2700-2704
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	37
Issue number	19
DOIs	https://doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P
State	Published - Oct 16 1998
Externally published	Yes

Keywords

Antibiotics
Eremomycin
Natural products
Total synthesis
Vancomycin

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Cite this

@article{078f097a0fa1488eb4da6ff6ab1dbc1e,

title = "Total syntheses of vancomycin and eremomycin aglycons",

abstract = "Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin-resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations.",

keywords = "Antibiotics, Eremomycin, Natural products, Total synthesis, Vancomycin",

author = "Evans, {David A.} and Wood, {Michael R.} and Trotter, {B. Wesley} and Richardson, {Timothy I.} and Barrow, {James C.} and Katz, {Jeffrey L.}",

year = "1998",

month = oct,

day = "16",

doi = "10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P",

language = "English (US)",

volume = "37",

pages = "2700--2704",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "19",

}

TY - JOUR

T1 - Total syntheses of vancomycin and eremomycin aglycons

AU - Evans, David A.

AU - Wood, Michael R.

AU - Trotter, B. Wesley

AU - Richardson, Timothy I.

AU - Barrow, James C.

AU - Katz, Jeffrey L.

PY - 1998/10/16

Y1 - 1998/10/16

N2 - Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin-resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations.

AB - Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin-resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations.

KW - Antibiotics

KW - Eremomycin

KW - Natural products

KW - Total synthesis

KW - Vancomycin

UR - http://www.scopus.com/inward/record.url?scp=0032538575&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032538575&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

DO - 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

M3 - Article

AN - SCOPUS:0032538575

SN - 1433-7851

VL - 37

SP - 2700

EP - 2704

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 19

ER -

Total syntheses of vancomycin and eremomycin aglycons

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this