1,2-Dichlorobenzene → (2'S,3'R,4'S,5'S,6'R)-6-chloro-5-(4-ethylbenzyl)-3',4',5'-trihydroxy-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-2H-spiro[benzofuran-3,2'-pyran]-2-one

Participants

Reaction Steps

To a solution of 48 (5 mg, 6.3 μmol) in a mixture of MeOH (1.5 mL) and THF (0.5 mL) were added Pd(OH)2/C (10 mg) and 1,2-dichlorobenzene (12 μL). A balloon of hydrogen gas was attached for 0.5 h with vigorous stirring. LCMS indicated that de-protection was complete. The reaction mixture was filtered through Celite, concentrated to a residue, and purified by passing through silica gel in a pipette (5% MeOH in DCM) to give 49 (2.2 mg, 80%). 1H NMR (300 MHz, CD3OD) δ 7.35 (s, 1H), 7.20 (s, 1H), 7.09 (s, 4H), 4.24-4.29 (m, 1H), 4.07 (t, J=10.5 Hz, 1H), 4.06 (s, 2H), 3.81 (dd, J=2.1, 12.0 Hz, 1H), 3.61-3.71 (m, 2H), 3.43 (t, J=9.9 Hz, 1H), 2.59 (q, J=7.5 Hz, 2H), 1.20 (t, J=7.5 Hz, 3H).

Provenance & Evidence