Citation: Shi-Sheng Wang, Li-Juan Luo, Zhi-Gang Gao, Tong-Wei Guan, Wei-Jie Zhao. A convenient synthesis of 2β, 3α-dihydroxyurs-12-en-28-oic acid as a natural diastereoisomer of corosolic acid[J]. Chinese Chemical Letters, ;2013, 24(07): 617-618. shu

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

1.
School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116023, China

Corresponding author: Shi-Sheng Wang,
Received Date: 10 January 2013
Available Online: 28 March 2013

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.
- 2β,3α-Dihydroxyurs-12-en-28-oic acid,
- Ursolic acid,
- Glycogen phosphorylase,
- Corosolic acid
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  [15] Spectra data of compound 3 (urs-2,12-dien-28-oic acid benzyl ester): ESI-MS:m/z 529.3 [M+H]⁺. ¹H NMR(400 MHz, CDC_l3): δ 0.71, 1.00, 1.08, 1.10, 1.25 (s, each 3H), 0.86 (d, 3H, J=5.6 Hz), 0.94 (d, 3H, J=6.90 Hz), 4.99 and 5.09 (d, each 1H, J=12.5 Hz), 5.26 (s, 1H), 5.37 and 5.41 (d, each 1H, J=10.2 Hz), 7.33 (m, 5H).
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  [16] Spectra data of compound 4 (2α,3α-epoxyurs-12-en-28-oic acid benzyl ester): ESI-MS:m/z 545.4 [M+H]⁺. ¹H NMR (400 MHz, CDC_l3): δ 0.61, 1.00, 1.08, 1.10, 1.25 (s, each 3H), 0.86 (d, 3H, J=6.4 Hz), 0.92 (d, 3H, J=5.6 Hz), 2.78 (d, 1H, J=3.5 Hz), 3.18 (1H, m), 4.99 and 5.08 (d, each 1H, J=12.5 Hz), 5.25 (s, 1H), 7.33 (m, 5H).
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  [17] Spectra data of compound 5 (2β,3α-dihydroxyurs-12-en-28-oic acid benzyl ester): ESI-MS: m/z 563.4 [M+H]⁺. ¹H NMR (400 MHz, CDC_l3): δ 0.62, 0.99, 1.06, 1.25, 1.27 (s, each 3H), 0.84 (d, 3H, J=6.0 Hz), 0.92 (d, 3H, J=5.6 Hz), 3.63 (d, 1H, J=10.3 Hz), 3.71 (m, 1H), 4.99 and 5.08 (d, each 1H, J=12.5 Hz), 5.25 (s, 1H), 7.33 (m, 5H).
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沈阳化工大学材料科学与工程学院沈阳 110142