Acetogenins of annonaceae. Part 86: synthesis of a highly functionalized precursor of (-)-4-deoxygigantecin, an annonaceous acetogenin

作者：Szlosek M; Peyrat JF; Chaboche C; Franck X; Hocquemiller R; Figadere B^*

来源：New Journal of Chemistry, 2000, 24(5): 337-342.

DOI：10.1039/b000236o

A highly functionalized precursor of(-)-4-deoxygigantecin possessing six stereogenic centers has been prepared in 14 steps from tridecanal. The key steps are (i) enantioselective aldolization, (ii) diastereoselective C-glycosylation and (iii) diastereoselective aldolization reactions, all of them using 2-trimethylsilyloxyfuran as nucleophile. This strategy would allow us to prepare squamostatin D as well, another acetogenin of Annonaceae possessing two nonadjacent tetrahydrofuran rings and a closely related tetrahydrofuran pattern.

• 出版日期2000-5