Sodium Benzoate → (+)-Pancratistatin

HRID 1779706Notes

Reaction equation

HRID 1779706 reaction equation
C(O[C:6]([NH:8][C@H:9]1[C@H:14]([OH:15])[C@H:13]([OH:16])[C@@H:12]2[O:17][C@@H:11]2[C@@H:10]1[C:18]1[C:19](C(OC)=O)=[C:20]([O:27]CC2C=CC=CC=2)[C:21]2[O:25][CH2:24][O:23][C:22]=2[CH:26]=1)=[O:7])(C)(C)C.C([O-])(=[O:46])C1C=CC=CC=1.[Na+]>O>[CH:26]1[C:18]2[C@H:10]3[C@@H:11]([OH:46])[C@H:12]([OH:17])[C@@H:13]([OH:16])[C@@H:14]([OH:15])[C@@H:9]3[NH:8][C:6](=[O:7])[C:19]=2[C:20]([OH:27])=[C:21]2[O:25][CH2:24][O:23][C:22]=12

Participants

4

Reactant 2

HCID 517055Sodium BenzoateHCID 10973444HCID 10973444, compound

Product 1

HCID 441597(+)-PancratistatinYield 1,550.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of epoxide 16 (109 mg, 0.21 mmol) and sodium benzoate (1 mg) in water (8 ml) was stirred at 100° C. for 6 days. The mixture was then concentrated and subjected to chromatography (CHCl3 /CH3OH, 4:1) to afford 35 mg (51%) of pancratistatin. 1H NMR (400 MHz, DMSO-d6) ε 13.06 (s, 1H), 7.51 (s, 1H), 6.48 (s, 1H), 6.05 (d, J=1.0 Hz, 1H), 6.02 (d, J=1.0 Hz, 1H), 5.35 (bs, 1H), 5.04 (bs, 2H), 4.84 (bs, 1H), 4.27 (bs, 1H), 3.95 (bs, 1H), 3.84 (bs, 1H), 3.74 (m, 2H), 2.96 (d, J=11.5 Hz, 1H).

Workup

  1. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-9496b245094e436e960c75e828bc9ba5
Source dataset
uspto-grants-1997_05
Patent number
US05627280

Reaction notes

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