Tetrahedron

Studies on the synthesis of the quartromicins: partial stereochemical assignment of quartromicins A 3 and D 3 and diastereoselective synthesis of the endo-and exo- …

WR Roush, DA Barda, C Limberakis, RK Kunz

Index: Roush, William R; Barda, David A; Limberakis, Chris; Kunz, Roxanne K Tetrahedron, 2002 , vol. 58, # 32 p. 6433 - 6454

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Citation Number: 30

Abstract

A partial stereochemical assignment of quartromicins A3 and D3 is presented, along with diastereoselective syntheses of the endo-and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of the proposed quartromicin stereostructure. The key steps of these syntheses are highly enantio-and diastereoselective Lewis acid catalyzed Diels–Alder reactions of 1, 1, 3, 4-tetrasubstituted diene 24.