LIGNANS .19. TOTAL SYNTHESIS OF (-)-O-DIMETHYLSUGIRESINOL, INVOLVING ASYMMETRIC [4-O-SILYL DERIVATIVE OF (D)-ERYTHRONOLACTONE(2]HETEROCYCLOADDITION OF A STYRENE WITH A BENZYLIDENEPYRUVIC ESTER OF AN ALPHA)

Authors
BROWN E DUJARDIN G MAUDET M
Citation
E. Brown et al., LIGNANS .19. TOTAL SYNTHESIS OF (-)-O-DIMETHYLSUGIRESINOL, INVOLVING ASYMMETRIC [4-O-SILYL DERIVATIVE OF (D)-ERYTHRONOLACTONE(2]HETEROCYCLOADDITION OF A STYRENE WITH A BENZYLIDENEPYRUVIC ESTER OF AN ALPHA), Tetrahedron, 53(28), 1997, pp. 9679-9694
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
28
Year of publication
1997
Pages
9679 - 9694
Database
ISI
SICI code
0040-4020(1997)53:28<9679:L.TSO(>2.0.ZU;2-K
Abstract
alpha-O-t-Butyldiphenylsilyl-(D)-erythronolactone [(+/-)-25] (a new ch iral vector) was esterified with 4-methoxybenzylidene pyruvic acid (19 ). Eu(fod)(3) catalyzed [4+2] heterocycloaddition of the latter 1-oxab utadiene with 4-methoxystyrene (as the dienophile), afforded high yiel ds of the endo adduct 23c with 95/5 diastereofacial ratio. Five furthe r steps led to enantiomerically pure natural (-)-O-dimethylsugiresinol (-)-2 in 12% overall yield from the acid 19. (C) 1997 Elsevier Scienc e Ltd.