SYNTHESIS OF UNDECULOFURANOSIDE DERIVATIVES OF THE HERBICIDINS AND OFANALOGS

The condensation of sopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the l ithium enolate of o-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one ( derived in six steps (25%) from the Diels-Alder adduct of furan to 1-c yanovinyl acetate) was highly exo face selective giving two major aldo ls that were separated readily. One of them was converted to ino-L-ido -7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis impli es the acid-promoted isomerization of nyl)selenomethyl]-beta-L-ido-L-i do-undecofuranose.