Journal of the American Chemical Society p. 6304 - 6311 (1980)
Update date:2022-08-05
Topics:
Jung, Michael E.
Shaw, Teresa J.
Ascorbic acid (Vitamin C) (9) is shown to be a useful, inexpensive chiral starting material for natural products synthesis.It is converted in high yield via two synthetic operations into (R)-glycerol acetonide (7), the more inaccessible enantiomer of glycerol acetonide.Since D-(R)-glyceraldehyde acetonide (4) and the corresponding alcohol 1 have been used in many total syntheses of a wide variety of compounds, the ready availability of the opposite enantiomers L-(S)-glyceraldehyde acetonide (6) and glycerol (7) should be of greate value.As one indication of this potential synthetic utility, the hypotensive, antiepileptic compound (R)-(-)-γ-amino-β-hydroxybutyric acid (GABOB) (8) has been synthesized from ascorbic acid (9) via nine steps in 10percent overall yield.As further evidence of the importance of these synthesis, several useful intermediates for the preparation of the highly active hypotensive agents, the aryloxypropanolamines (5), were prepared from Vitamin C.
View MoreBeijing Merson Pharmaceutical Co., Ltd
Contact:0086-10-80484934 0086-10-80484574/
Address:2nd Floor , No. 2 Building , No. 14 Houshayu Duan, Jingmi Road ,Shunyi District , Beijing 101318, P.R.China
Suzhou Chiral Pharmaceuticals Co., Ltd.
Contact:86-0512-63197058
Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
Contact:+852-8198 2399
Address:9E, Leapont Industrial Building, 18-28 Wo Liu Hang Road, Shatin, New Territories, Hong Kong
Contact:+86-0512-69209969
Address:Room 317,Lushan Road,Suzhou New District,Jiangsu Province,China.
Jiangyin Tenghua Import&Export Co.,Ltd.
Contact:+86-510-86263875
Address:Room 402-B,9 Yanling Road, Jiangyin,Jiangsu, China
Doi:10.1007/s10593-019-02565-8
(2019)Doi:10.1002/jms.4024
(2017)Doi:10.1021/ja00538a049
(1980)Doi:10.1016/j.bmcl.2004.06.098
(2004)Doi:10.1016/0040-4020(95)98706-N
(1995)Doi:10.1016/0022-328X(86)80439-9
(1986)