Tetrahedron

A concise route to a key intermediate in the total syntheses of (+)-tirandamycic acid and (-)-tirandamycin a†

SF Martin, C Gluchowski, CL Campbell, RC Chapman

文献索引：Martin, Stephen F.; Gluchowski, Charles; Campbell, Carlton L.; Chapman, Robert C. Tetrahedron, 1988 , vol. 44, # 11 p. 3171 - 3180

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被引用次数: 35

摘要

An efficacious, asymmetric synthesis of the 2, 9-dioxabicyclo [3, 3, 1] nonane 4 has been completed in nine chemical steps from 4, 5-dimethylfuraldehyde (8). Since enantiomerically pure 4 has been previously converted in five steps by Ireland into (+)-tirandamycic acid (3) and more recently by Schlessinger into (-)-tirandamycin A (1), this achievement constitutes in a strictly formal sense the total syntheses of these substances. The key step in the ...