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, n
o11, pp. 2072-2075 [4 page(s) (article)]
Langue / Language
Anglais
Editeur / Publisher
American Society of Pharmacognosy, Northbrook, IL, ETATS-UNIS
(1979)
(Revue)
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Localisation / Location
INIST-CNRS, Cote INIST : 4127, 35400018658774.0330
Nº notice refdoc (ud4) : 22189893
