Synthesis of heterocyclic systems with a carbohydrate fragment

Reactions of 3-iodolevoglucosenone with sodium derivatives of some CH acids. Chiral cyclopropanes and stable oxetenes

“…The reaction mixture was stirred for 20 rain and quenched by adding a 39b aqueous solution of HCI to pH 7. and the prodt,ct was extracted with CH2CI 2 (3x5 mL). The combined extracts were washed with brine, dried with MgSO4, concentrated, and chromatographed (AcOEt--heptane (13). An ozone--oxygen mixture was passed for 5 rain at 0 ~ through a solution of oxetene 12 (0.25 g) in 10 mL of CHCI 3 (TLC monitoring).…”