Asymmetric total synthesis of (+)-cardiobutanolide via an iterative asymmetric dihydroxylation in PEG

被引：9

作者：

Chandrasekhar, S. ^{[1
]}

Kiranmai, N. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 31期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; ACETOGENINS; STYRYLLACTONE;

D O I：

10.1016/j.tetlet.2010.05.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective total synthesis of (+)-cardiobutanolide, a polyhydroxylated natural product, is achieved in high yield through Lu and Guo diene synthesis. Sharpless asymmetric dihydroxylation, and one-pot deprotection-lactonization. The utility of a recyclable reagent system in PEG for asymmetric dihydroxylation is demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4058 / 4060

页数：3

共 20 条

[1] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[2]

[Anonymous], 1991, REDUCTIONS ALUMINO B

[3]

Blázquez MA, 1999, PHYTOCHEM ANALYSIS, V10, P161, DOI 10.1002/(SICI)1099-1565(199907/08)10:4<161::AID-PCA453>3.0.CO

[4]

2-2

[5]

Cave A, 1997, Fortschr Chem Org Naturst, V70, P81

[6] Osmium tetroxide in poly(ethylene glycol) (PEG): a recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, NR .

CHEMICAL COMMUNICATIONS, 2003, (14) :1716-1717

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

Garg, Ashish ;

Singh, Ravi P. ;

Singh, Vinod K. .

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

[8] A NOVEL DEOXYGENATION-ISOMERIZATION REACTION OF 4-HYDROXY-2-YNOIC ESTERS AND GAMMA-HYDROXY-ALPHA,BETA-YNONES [J].

GUO, C ;

LU, XY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :394-395

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

Hisham, A ;

Toubi, M ;

Shuaily, W ;

Bai, MDA ;

Fujimoto, Y .

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

[10] Stereoselective total synthesis of (+)-cardiobutanolide and (+)-3-epi-cardiobutanolide from diacetone D-glucose [J].

Krishna, Palakodety Radha ;

Reddy, P. V. Narsimha .

TETRAHEDRON LETTERS, 2006, 47 (27) :4627-4630

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