Pyridine → 5,7-Dihydroxy-1,5,5a,11a,13a-pentamethyl-4,8-dioxo-4,5,5a,5b,6,6a,6b,7,8,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-icosahydro-1H-oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-6,11,12,13-tetrayl tetraacetate

HRID 525291Notes

Reaction equation

[CH3:1][C@H:2]1[C@@H:7]2[C@@:8]3([CH3:40])[C@@H:15]([O:16][C:17]([CH3:19])=[O:18])[C@@H:14]([O:20][C:21]([CH3:23])=[O:22])[C@@H:13]4[C@@:24]5([CH3:39])[C@@H:29]([O:30][C:31]([CH3:33])=[O:32])[C@H:28]6[O:34][C@H:27]6[CH2:26][C@@H:25]5[C:35]([C@H:37]([OH:38])[C@H:12]4[C@@H:9]3[C@@H:10]([OH:11])[C@H:6]2[C@@:5]2([CH3:47])[C@@:41]([OH:46])([CH3:45])[C:42]([O:44][C:4]2=[CH:3]1)=[O:43])=[O:36].N1C=CC=CC=1.[C:54](OC(=O)C)(=[O:56])[CH3:55]>>[CH3:1][C@H:2]1[C@@H:7]2[C@@:8]3([CH3:40])[C@@H:15]([O:16][C:17]([CH3:19])=[O:18])[C@@H:14]([O:20][C:21]([CH3:23])=[O:22])[C@@H:13]4[C@@:24]5([CH3:39])[C@@H:29]([O:30][C:31]([CH3:33])=[O:32])[C@H:28]6[O:34][C@H:27]6[CH2:26][C@@H:25]5[C:35]([C@H:37]([OH:38])[C@H:12]4[C@@H:9]3[C@@H:10]([O:11][C:54]([CH3:55])=[O:56])[C@H:6]2[C@@:5]2([CH3:47])[C@@:41]([OH:46])([CH3:45])[C:42]([O:44][C:4]2=[CH:3]1)=[O:43])=[O:36]

Participants

Reactant 3

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 56662029Taccalonolide B

Product 1

HCID 4416855,7-Dihydroxy-1,5,5a,11a,13a-pentamethyl-4,8-dioxo-4,5,5a,5b,6,6a,6b,7,8,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-icosahydro-1H-oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-6,11,12,13-tetrayl tetraacetate

Procedure

Taccalonolide B (3 mg) was dissolved in 0.3 mL of acetic anhydride. To this solution, 0.3 mL of anhydrous pyridine was added and was kept at room temperature for 48 h. The reaction solution was dried in miVac and separated using C18 HPLC to yield taccalonolide A and TB-Ac-16.

Workup

customThe reaction solution was dried in miVac
customseparated

Sources & evidence

ORD record: ord-8a5b830395c34542b8e4bd8391909847
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340572B2

Reaction notes

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