Multigram synthesis of glyceollin I

…, M Reese, J Liu, M El-Dakdouki, N Malik…

Index: Luniwal, Amarjit; Malik, Neha; Erhardt, Paul; Khupse, Rahul; Reese, Michael; Liu, Jidong; El-Dakdouki, Mohammad; Fang, Lei Organic Process Research and Development, 2011 , vol. 15, # 5 p. 1149 - 1162

Full Text: HTML

Citation Number: 10

Abstract

Scaled-up procedures and preparation of glyceollin I in multigram quantities are described. The synthesis features construction of a cis-fused ring system in high enantiomeric excess after Sharpless asymmetric dihydroxylation of a key intermediate that is initially produced by an intramolecular Wittig reaction to afford the requisite alkene while simultaneously forming the first ring. The overall yield is 12% after 11 steps.

Related Articles:

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

[Kagawa, Hitoshi; Shigematsu, Asako; Ohta, Shigeru; Harigaya, Yoshihiro Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 5 p. 547 - 554]

Cobalt schiff base complex promoted retro-claisen reaction of 1-(2-hydroxyphenyl)-3-phenyl-1, 3-propanediones and flavone formation

[Nishinaga, Akira; Maruyama, Kazushige; Ando, Hiroyuki; Sato, Ryoji; Mashino, Takahiro; Inada, Akira; Nakanishi, Tsutomu Tetrahedron Letters, 1990 , vol. 31, # 22 p. 3171 - 3174]

Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities

[Zhao, Wei; Sun, Jie; Xiang, Hua; Zeng, Yan-Yan; Li, Xiao-Bo; Xiao, Hong; Chen, De-Ying; Ma, Ren-Ling Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 10 p. 3192 - 3203]

More Articles...