A convenient synthesis of 2β,3α-dihydroxyurs-12-en-28-oic acid as a natural diastereoisomer of corosolic acid

A convenient synthesis of 2β,3α-dihydroxyurs-12-en-28-oic acid as a natural diastereoisomer of corosolic acid

2β,3α--Dihydroxyurs-12-en-28-oic acid （6） is a naturally occurring diastereoisomer of corosolic acid with glycogen phosphorylase inhibitory activity. A new strategy for the semi-synthesis of 6 was developed. Using the commercially available ursolic acid （1） as the starting materials, 6 was synthesiz...

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Veröffentlicht in:Chinese chemical letters 2013-07, Vol.24 (7), p.617-618
Hauptverfasser: Wang, Shi-Sheng, Luo, Li-Juan, Gao, Zhi-Gang, Guan, Tong-Wei, Zhao, Wei-Jie
Format: Artikel
Sprache:eng
Schlagworte:
2β,3α-Dihydroxyurs-12-en-28-oic acid
Corosolic acid
ESI-MS
Glycogen phosphorylase
NMR
Ursolic acid
半合成
天然
抑制活性
立体选择性
糖原磷酸化酶
非对映异构体
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Zusammenfassung:2β,3α--Dihydroxyurs-12-en-28-oic acid （6） is a naturally occurring diastereoisomer of corosolic acid with glycogen phosphorylase inhibitory activity. A new strategy for the semi-synthesis of 6 was developed. Using the commercially available ursolic acid （1） as the starting materials, 6 was synthesized through five facile reactions with a high stereoselectivity and an overall yield of 47,3%, The structure of 6 was confirmed by optical rotation, ESI-MS, 1H NMR and 13C NMR data,
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2013.04.022