Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The first enantioselective synthesis of trans-(6aS, 11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS, 11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2′-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.

Original languageEnglish
Pages (from-to)558-563
Number of pages6
JournalChirality
Volume15
Issue number6
DOIs
Publication statusPublished - 2003

Fingerprint

Pterocarpans
Stereochemistry
X ray analysis
Skeleton
Spectroscopy
Derivatives
Spectrum Analysis
X-Rays

Keywords

  • 2,3-dihydrobenzo [b]furan
  • Asymmetric synthesis
  • Chromane
  • Configurational assignment
  • Helicity rule

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton. / Kiss, L.; Kurtán, T.; Antus, S.; Bényei, A.

In: Chirality, Vol. 15, No. 6, 2003, p. 558-563.

Research output: Contribution to journalArticle

@article{1a54d51e2e28421384240311e303ce2f,
title = "Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton",
abstract = "The first enantioselective synthesis of trans-(6aS, 11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS, 11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2′-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.",
keywords = "2,3-dihydrobenzo [b]furan, Asymmetric synthesis, Chromane, Configurational assignment, Helicity rule",
author = "L. Kiss and T. Kurt{\'a}n and S. Antus and A. B{\'e}nyei",
year = "2003",
doi = "10.1002/chir.10235",
language = "English",
volume = "15",
pages = "558--563",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "6",

}

TY - JOUR

T1 - Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton

AU - Kiss, L.

AU - Kurtán, T.

AU - Antus, S.

AU - Bényei, A.

PY - 2003

Y1 - 2003

N2 - The first enantioselective synthesis of trans-(6aS, 11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS, 11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2′-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.

AB - The first enantioselective synthesis of trans-(6aS, 11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS, 11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2′-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.

KW - 2,3-dihydrobenzo [b]furan

KW - Asymmetric synthesis

KW - Chromane

KW - Configurational assignment

KW - Helicity rule

UR - http://www.scopus.com/inward/record.url?scp=0038650506&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0038650506&partnerID=8YFLogxK

U2 - 10.1002/chir.10235

DO - 10.1002/chir.10235

M3 - Article

C2 - 12774295

AN - SCOPUS:0038650506

VL - 15

SP - 558

EP - 563

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 6

ER -