SYNTHESIS AND APPLICATION OF 3,3-SPIROCYCLOPROPANE DERIVATIVES OBTAINED FROM 1,2 5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE/

3,3-Spirocyclopropane derivatives (5 and 7) were prepared by three dif ferent methods of cyclopropanation starting from 1,2:5,6-di-O-isopropy lidene-alpha-D-glucofuranose (2). Subsequent radical induced cycloprop ane ring opening reaction stereospecifically provided the 3-C-allyl de rivative (9). However, activation of the cyclopropyl ring through the aldehyde (10) followed by hydrogenation gave a quaternary chiral deriv ative (11) which was elaborated to the versatile intermediate (1) by u sing Bamford-Stevens reaction.