Progress in the Synthesis of the Lituarines: Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template
2005; American Chemical Society; Volume: 7; Issue: 22 Linguagem: Inglês
10.1021/ol0520018
ISSN1523-7060
AutoresJeremy Robertson, Jonathan W. P. Dallimore,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoWe describe elaboration of a tricyclic spirobutenolide corresponding to the C(7−18) tricyclic substructure common to lituarines A−C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18−19) bond by silyl enol ether addition to the derived spiroacetal C(18)−O oxonium ion. Esterification with a C(1−6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.
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