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Lignans.19. Total synthesis of (−)-O-dimethylsugiresinol, involving asymmetric [4+2] heterocycloaddition of a styrene with a benzylidenepyruvic ester of an α-O-silyl derivative of (D)-erythronolactone

✍ Scribed by Eric Brown; Gilles Dujardin; Mickaël Maudet


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
908 KB
Volume
53
Category
Article
ISSN
0040-4020

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📜 SIMILAR VOLUMES


Asymmetric endoselective [4+2] heterocyc
✍ Gilles Dujardin; Mickaël Maudet; Eric Brown 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 217 KB

Eu(fod) 3 catalyzed [4+2] heterocycloadditions ofpara-methoxystyrene 7 with esters 8a-f of benzylidenepyruvic acids (deriving from various chiral alcohols) furnished endo adducts 9a-f with variable diastereoselective ratios (from 58/42 to 86/14). Interestingly, the benzylidenepyruvic esters 8g and 8