HRID1285478

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COc1cc([C@@H]2c3cc4c(cc3[C@H](O)[C@H]3COC(=O)[C@@H]23)OCO4)cc(OC)c1OC

HCID72435

Picropodophyllin

C22H22O8

结构：CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C

HCID590018

TBDMS ether

C12H30OSi2

PRODUCTS

生成物

HCID10607

Podofilox

C22H22O8

收率 36%

HCID72435

Picropodophyllin

C22H22O8

收率 34%

PROCEDURE

实验过程

In an improvement of the Gensler epimerization, picropodophyllotoxin was converted to the t-butyldimethylsilyl ether. Formation of the enolate with LDA, irreversible quenching with pyridine hydrochloride followed by desilylation afforded 36% podophyllotoxin and 34% picropodophyllotoxin.

WORKUP

后处理

customFormation of the enolate with LDA, irreversible quenching with pyridine hydrochloride

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ba41022d396a43ef99ef243c2185a59a
来源数据集: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04567253
来源说明: uspto-grants-1986_01

反应 SMILES

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:13]2[C@@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Si](O[Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C>>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10].[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C@H:13]2[C@@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]