Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis

被引：18

作者：

Chojnacka, Kinga ^{[1
]}

Santoro, Stefano ^{[2
]}

Awartani, Radi ^{[3
]}

Richards, Nigel G. J. ^{[1
]}

Himo, Fahmi ^{[2
]}

Aponick, Aaron ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

[2] Stockholm Univ, Dept Organ Chem, SE-10691 Stockholm, Sweden

[3] Petra Res Inc, Alachua, FL 32615 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 15期

基金：

瑞典研究理事会; 美国国家科学基金会;

关键词：

ARBUSCULAR MYCORRHIZAL FUNGI; ROOT PARASITIC WEEDS; GERMINATION STIMULANTS; TERPENE BIOSYNTHESIS; PLANT BIOREGULATORS; OROBANCHE; PATHWAY; STRIGA; BENZALDEHYDES; ARABIDOPSIS;

D O I：

10.1039/c1ob05751k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a new method for constructing the ABC ring system of strigolactones, in a single step from a simple linear precursor by acid-catalyzed double cyclization. The reaction proceeds with a high degree of stereochemical control, which can be qualitatively rationalized using DFT calculations. Our concise synthetic approach offers a new model for thinking about the (as yet) unknown chemistry that is employed in the biosynthetic pathways leading to this class of plant hormones.

引用

页码：5350 / 5353

页数：4

共 38 条

[31] Synthetic disproof of the structure proposed for solanacol, the germination stimulant for seeds of root parasitic weeds [J].