HCID 68792675, compound → HCID 24853496, compound

Participants

Reaction Steps

(2′S,3′R,4′S,5′R,6′R)-6′-(Acetoxymethyl)-7-chloro-6-(4-ethylbenzyl)-3′,4′,5′,6′-tetrahydrospiro[chroman-4,2′-pyran]-3′,4′,5′-triyl triacetate (19) (9.6 mg, 0.02 mmol) was dissolved in MeOH (0.2 mL) and treated with LiOMe (20 μL of a 1M solution in MeOH). After 24 h, the reaction mixture was filtered through a syringe filter and concentrated, then passed through a small SiO2 column, eluting with 5% MeOH/CH2Cl2 to provide a film (5.8 mg, 83%). 1H NMR (300 MHz, CD3OD) δ ppm: 7.37 (s, 1H), 7.05 (s, 4H), 6.79 (s, 1H), 4.33 (m, 1H), 4.13 (m, 1H), 3.97 (s, 2H), 3.78 (m, 2H), 3.48-3.62 (m, 3H), 3.33 (m, 2H), 2.57 (q, J=15, 7.8 Hz, 2H), 2.33-2.42 (m, 1H), 2.13-2.21 (m, 1H), 1.19 (t, J=7.5 Hz, 3H). LC/MS 100% (ELSD) tR=1.99 min, calcd for C23H27ClO6: 434.15, found 434.15 (M+Na)+.

Provenance & Evidence