81969-33-7Relevant academic research and scientific papers
Chiral lactols, XIV: Stereoselective fusion of five-membered ring lactols to the bornane ring system
Noe, Christian R.,Knollmueller, Max,Gaertner, Peter,Mereiter, Kurt,Steinbauer, Gerhard
, p. 1015 - 1021 (2007/10/03)
Condensation of d-camphor (1) with diethyl oxalate and subsequent ester hydrolysis yielded camphoroxalic acid 3. endo-Fused lactone 9 was obtained by reduction of 3 with zinc followed by reduction with NaBH4 and ring closure with H2SO4. exo-Fused lactone 16, the crystal structure of which was determined, was prepared by reduction of 3 with NaBH4 under basic conditions followed by catalytic hydrogenation and ring closure with HCl. Reduction of 9 and 16 with DI-BALH and application of acidic work-up conditions yielded the self-condensed reduction products (lactol anhydrides) 10 and 17, which are useful reagents in racemate resolution and stereoselective synthesis. VCH Verlagsgesellschaft mbH, 1996.
