Ethyl Acetate → (2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-6-chloro-5-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-2H-spiro[benzofuran-3,2'-pyran]-2-one

Participants

Reaction Steps

To a solution of 27 (8 mg, 10 μmol) in DCM was added pyridinium chlorochromate (9 mg, 42 μmol, 4.2 equiv). The mixture was stirred for 5 days until the reaction was complete. The mixture was directly loaded onto a preparatory TLC plate and developed using 15% EtOAc in petroleum ether to give 48 (5 mg, 62% yield). 1H NMR (300 MHz, CDCl3) δ 7.00-7.40 (m, 25H), 6.76 (d, J=6.6 Hz, 2H), 4.80-4.92 (m, 3H), 4.64 (d, J=10.8 Hz, 1H), 4.38-4.57 (m, 5H), 3.92-4.03 (m, 3H), 3.71-3.82 (m, 3H), 3.60 (dd, J=1.8, 11.1 Hz, 1H), 2.57 (q, J=7.5 Hz, 2H), 1.18 (t, J=7.5 Hz, 3H).

Provenance & Evidence