Revision of the absolute configuration of salicylihalamide A through asymmetric total synthesis

Yusheng Wu, Lothar Esser, Jef K. De Brabander

Research output: Contribution to journalArticle

Abstract

A highly E-selective ring-closing metathesis is the key to building the macrocyclic salicylate core of (+)-salicylihalamide A (1). The synthesis results in a reassignment of the absolute configuration of natural (-)-salicylihalamide A (2), a structurally unprecedented antitumor metabolite with a potentially novel mode of action.

Original languageEnglish (US)
Pages (from-to)4308-4310
Number of pages3
JournalAngewandte Chemie - International Edition
Volume39
Issue number23
DOIs
StatePublished - Dec 4 2000

Fingerprint

Metabolites
Salicylates
salicylihalamide A

Keywords

  • Antitumor agents
  • Asymmetric synthesis
  • Configuration determination
  • Metathesis
  • Natural products

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Revision of the absolute configuration of salicylihalamide A through asymmetric total synthesis. / Wu, Yusheng; Esser, Lothar; De Brabander, Jef K.

In: Angewandte Chemie - International Edition, Vol. 39, No. 23, 04.12.2000, p. 4308-4310.

Research output: Contribution to journalArticle

@article{8f4757b4562d4e4ab330a90c47d35207,
title = "Revision of the absolute configuration of salicylihalamide A through asymmetric total synthesis",
abstract = "A highly E-selective ring-closing metathesis is the key to building the macrocyclic salicylate core of (+)-salicylihalamide A (1). The synthesis results in a reassignment of the absolute configuration of natural (-)-salicylihalamide A (2), a structurally unprecedented antitumor metabolite with a potentially novel mode of action.",
keywords = "Antitumor agents, Asymmetric synthesis, Configuration determination, Metathesis, Natural products",
author = "Yusheng Wu and Lothar Esser and {De Brabander}, {Jef K.}",
year = "2000",
month = "12",
day = "4",
doi = "10.1002/1521-3773(20001201)39:23<4262::AID-ANIE4262>3.0.CO;2-Y",
language = "English (US)",
volume = "39",
pages = "4308--4310",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "23",

}

TY - JOUR

T1 - Revision of the absolute configuration of salicylihalamide A through asymmetric total synthesis

AU - Wu, Yusheng

AU - Esser, Lothar

AU - De Brabander, Jef K.

PY - 2000/12/4

Y1 - 2000/12/4

N2 - A highly E-selective ring-closing metathesis is the key to building the macrocyclic salicylate core of (+)-salicylihalamide A (1). The synthesis results in a reassignment of the absolute configuration of natural (-)-salicylihalamide A (2), a structurally unprecedented antitumor metabolite with a potentially novel mode of action.

AB - A highly E-selective ring-closing metathesis is the key to building the macrocyclic salicylate core of (+)-salicylihalamide A (1). The synthesis results in a reassignment of the absolute configuration of natural (-)-salicylihalamide A (2), a structurally unprecedented antitumor metabolite with a potentially novel mode of action.

KW - Antitumor agents

KW - Asymmetric synthesis

KW - Configuration determination

KW - Metathesis

KW - Natural products

UR - http://www.scopus.com/inward/record.url?scp=85047694982&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85047694982&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20001201)39:23<4262::AID-ANIE4262>3.0.CO;2-Y

DO - 10.1002/1521-3773(20001201)39:23<4262::AID-ANIE4262>3.0.CO;2-Y

M3 - Article

AN - SCOPUS:85047694982

VL - 39

SP - 4308

EP - 4310

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 23

ER -