Journal of the American Chemical Society

Asymmetric Total Synthesis of e nt-(-)-Roseophilin: Assignment of Absolute Configuration

DL Boger, J Hong

文献索引：Boger; Hong Journal of the American Chemical Society, 2001 , vol. 123, # 35 p. 8515 - 8519

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被引用次数: 124

摘要

An asymmetric total synthesis of ent-(-)-roseophilin (1), the unnatural enantiomer of a novel naturally occurring antitumor antibiotic, is described. The approach enlists a room temperature heterocyclic azadiene inverse electron demand Diels-Alder reaction of dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylate (7) with the optically active enol ether 6 bearing the C23 chiral center followed by a reductive ring contraction reaction for formation of an ...