First total synthesis of (±)-celaphanol A

被引：5

作者：

Bie, PY ^{[1
]}

Zhang, CL ^{[1
]}

Li, AP ^{[1
]}

Peng, XJ ^{[1
]}

Wu, TX ^{[1
]}

Pan, XF ^{[1
]}

机构：

[1] Lanzhou Univ, Natl Lab Appl Organ Chem, Dept Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2002年 / 49卷 / 04期

关键词：

(+/-)-celaphanol A; diterpene; total synthesis;

D O I：

10.1002/jccs.200200089

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

The first total synthesis of (+/-)-Celaphanol A was accomplished starting from alpha-cyclocitral and 3,4-dimethoxy benzyl chloride in six steps. The intramolecular cyclization with BF3.Et2O and enolization in t-BuOK/t-BuOH were the key steps. The process of intramolecular cyclization afforded an all-cis isomer intermediate for synthesis of aromatic tricyclic diterpenes.

引用

页码：581 / 583

页数：3

共 7 条

[1]

BRUNING R, 1978, PHYTOCHEMISTRY, V17, P1821, DOI 10.1016/S0031-9422(00)88719-1

[2]

Triterpene caffeoyl esters and diterpenes from Celastrus stephanotifolius [J].

Chen, B ;

Duan, HQ ;

Takaishi, Y .

PHYTOCHEMISTRY, 1999, 51 (05) :683-687

[3]

Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether [J].

Gan, YH ;

Li, AP ;

Pan, XF ;

Chan, ASC ;

Yang, TK .

TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :781-787

[4]

GEUTAHAUN A, 1973, ECON BOT, V27, P353

[5]

KONDO Y, 1963, CHEM PHARM BULL, V11, P678

[6]

SHIZURI Y, 1973, TETRAHEDRON, V29, P1173

[7]

The first total synthesis of (+/-)-demethyl salvicanol [J].

Wang, XC ;

Pan, XF ;

Cui, YX ;

Chen, YZ .

TETRAHEDRON, 1996, 52 (32) :10659-10666

← 1 →