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Titre du document / Document title

Total Syntheses of Racemic and Natural Glycinol

Auteur(s) / Author(s)

LUNIWAL Amarjit (1) ; KHUPSE Rahul S. (1) ; REESE Michael (1) ; LEI FANG (1) ; ERHARDT Paul W. (1) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Center for Drug Design and Development, Department of Medicinal and Biological Chemistry, The University of Toledo College of Pharmacy, Toledo, Ohio 43606-3390, ETATS-UNIS

Résumé / Abstract

Total syntheses of racemic and (-)-glycinol (1) are described. A Wittig reaction produced the isoflav-3-ene from which a Sharpless dihydroxylation introduced either the racemic or enantiomeric 6a-hydroxy group. A 5.5% overall yield of racemic material was obtained after 12 steps. A method was devised for a one-pot switch of protecting groups masking a sensitive resorcinolic para-functionality, and conditions were optimized to prompt spontaneous closure of the pterocarpanolic dihydrofuran upon subsequent exposure of its ortho-functionality. These improvements eliminated two steps and increased the overall yield to 9.8% during production of the natural enantiomer.

Revue / Journal Title

Journal of natural products    ISSN  0163-3864   CODEN JNPRDF 

Source / Source

2009, vol. 72, no11, pp. 2072-2075 [4 page(s) (article)]

Langue / Language

Anglais

Editeur / Publisher

American Society of Pharmacognosy, Northbrook, IL, ETATS-UNIS  (1979) (Revue)

Mots-clés anglais / English Keywords

Chemical synthesis

;

Phenols

;

Flavonoid

;

Asymmetric synthesis

;

Phytoalexin

;

Racemic

;

Total synthesis

;

Mots-clés français / French Keywords

Benzofurobenzopyrane

;

Benzofuro[3,2-c][1]benzopyrane dérivé

;

Glycinol

;

Synthèse chimique

;

Phénols

;

Flavonoïde

;

Synthèse asymétrique

;

Phytoalexine

;

Racémique

;

Synthèse totale

;

Mots-clés espagnols / Spanish Keywords

Síntesis química

;

Fenoles

;

Flavonoide

;

Síntesis asimétrica

;

Fitoalexina

;

Racémico

;

Síntesis total

;

Localisation / Location

INIST-CNRS, Cote INIST : 4127, 35400018658774.0330

Nº notice refdoc (ud4) : 22189893



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