Stereoselective total synthesis of (+)-cardiobutanolide

被引：37

作者：

Prasad, Kavirayani R. ^{[1
]}

Gholap, Shivajirao L. ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 07期

关键词：

D O I：

10.1021/jo7025614

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from D-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylarnide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.

引用

页码：2916 / 2919

页数：4

共 22 条

[1]

BALOGH V, 1971, J ORG CHEM, V36, P1399

[2]

Blázquez MA, 1999, PHYTOCHEM ANALYSIS, V10, P161, DOI 10.1002/(SICI)1099-1565(199907/08)10:4&lt

[3]

161::AID-PCA453&gt

[4]

3.0.CO

[5]

2-2

[6] Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide [J].

Chandrasekhar, M ;

Chandra, KL ;

Singh, VK .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4039-4045

[7] TOTAL SYNTHESIS OF BOTH (+)-COMPACTIN AND (+)-MEVINOLIN - A GENERAL STRATEGY BASED ON THE USE OF A SPECIAL TITANIUM REAGENT FOR DICARBONYL COUPLING [J].

CLIVE, DLJ ;

MURTHY, KSK ;

WEE, AGH ;

PRASAD, JS ;

DASILVA, GVJ ;

MAJEWSKI, M ;

ANDERSON, PC ;

EVANS, CF ;

HAUGEN, RD ;

HEERZE, LD ;

BARRIE, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3018-3028

[8] OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].

COREY, EJ ;

ERICKSON, BW .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&

[9] Asymmetric synthesis of (+)-cardiobutanolide [J].

Garg, Ashish ;

Singh, Ravi P. ;

Singh, Vinod K. .

TETRAHEDRON, 2006, 62 (48) :11240-11244

[10] Cardiobutanolide, a styryllactone from Goniothalamus cardiopetalus [J].

Hisham, A ;

Toubi, M ;

Shuaily, W ;

Bai, MDA ;

Fujimoto, Y .

PHYTOCHEMISTRY, 2003, 62 (04) :597-600

← 1 2 3 →