Citation: Hong CHEN, Shao Yi SUN, De Quan YU. Stereoselective Addition of Organotitanium and Grignard Reagents to 3,5-O-isopropylidene-L-glucurono-γ-lactone[J]. Chinese Chemical Letters, ;1998, 9(10): 889-892. shu

Stereoselective Addition of Organotitanium and Grignard Reagents to 3,5-O-isopropylidene-L-glucurono-γ-lactone

Institute of Meteria Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050

Received Date: 23 April 1998

Fund Project: The work is supported by the National Science Foundation of China and the Doctoral Foundation of State Education Commission of China. We thank the Department of instrumental analysis of our institute for IR,MS, ¹HNMR and [α] measurement.

Substituted PhMgX and PhTi (OCHMe₂)₄MgX react with 3,5-O-isopropylidene-L-glucurono-γ-lactone 4 to give tetraols 5_a~e and its stereoisomers 6_a~e. Tetraols 5_a~e are the important intermediates in the synthesis of howiinol A1 and its derivatives. The stereoselectivities of substituted PhTi (OCHMe₂)₄Mg (5_a~e:6_a~e ratio, 68~72:32~28) were better than those of substituted PhMgX (33~64:67~36) in the reaction. The effects of different substituted groups and positions (p-Me, m-Me, o-MeO, p-Cl) of the phenyl ring on their stereoselectivies were not significant.
- Organotitanium reagents,
- Stereoselective reaction,
- 3,5-O-isopropylidene-L-glucurono-γ-lactone
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