Yin Xueqiang, Zhao Guoxia, Schneller Stewart W
Department of Chemistry and Biochemistry, Auburn University Auburn, Alabama 36849-5312.
Tetrahedron Lett. 2007 Jul 9;48(28):4809-4811. doi: 10.1016/j.tetlet.2007.05.079.
(3aS,4S,6R,6aR)-Tetrahydro-2,2-dimethyl-6-vinyl-3aH-cyclopenta[d][1,3]-dioxol-4-ol, itself available from ribose, provided a convenient entry point for an 18-step preparation of carbocyclic sinefungin. This procedure is adaptable to a number of carbocyclic sinefungin analogs with diversity of heterocyclic base and in the amino acid bearing side chain.
(3aS,4S,6R,6aR)-四氢-2,2-二甲基-6-乙烯基-3aH-环戊二烯并[d][1,3]-二氧戊环-4-醇本身可由核糖制得,为18步制备碳环型西奈芬净提供了一个便捷的切入点。该方法适用于多种具有杂环碱基多样性和含氨基酸侧链的碳环型西奈芬净类似物。