Chiral decalins: Preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox
文献类型：期刊论文
| 作者 | Yang, HJ ; Li, BG ; Cai, XH ; Qi, HY ; Luo, YG ; Zhang, GL |
| 刊名 | JOURNAL OF NATURAL PRODUCTS
 |
| 出版日期 | 2006 |
| 卷号 | 69期号:11页码:1531_1538 |
| ISSN号 | 0163-3864 |
| 产权排序 | 1 |
| 通讯作者 | Zhang, GL, Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China. |
| 中文摘要 | A novel and versatile process was developed to prepare the trans-decalins Delta(9(11))-3 beta-acetoxysclareolide (2) and Delta(9(11)3)- acetoxy-8-epi-sclareolide (3), respectively, with 4a-methoxycarbonyl-2,7,7-trimethyl-1-oxo-cis-decalin-2-ene (4) and its C-3 hydroxyl derivative 5 from oleanolic acid (3 beta-hydroxyolean-12-en-28-oic acid, 1). Three key steps were (a) introduction of the AcO-12 group and the C-9, C-11 double bond at ring C of methyl 3 beta-acetoxyolean-12-en-28-oate (8) to afford the diene, methyl 3,12-diacetoxyolean-9(11), 12-dien-28-oate (11); (b) photolytic cleavage of the C-8, C-14 bond in the diene to give an acetoxy-substituted triene 14; and (c) oxidative cleavage of the triene or its hydrolyzed alpha,beta-unsaturated ketone product with m-CPBA/TsOH to give the cis- and trans-decalins 2-5.Delta(9(11))-3 beta-Acetoxysclareolide (2) was stereospecifically reduced to give 3 beta-acetoxy-9-epi-sclareolide (23), from which (-)- 9-epi-ambrox (7) was synthesized. |
| 学科主题 | Plant Sciences; Chemistry, Medicinal; Pharmacology & Pharmacy |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000242298300001 |
| 公开日期 | 2011-07-08 |
| 源URL | [http://210.75.237.14/handle/351003/17773]  |
| 专题 | 成都生物研究所_天然产物研究 |
| 推荐引用方式 GB/T 7714 | Yang, HJ,Li, BG,Cai, XH,et al. Chiral decalins: Preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox[J]. JOURNAL OF NATURAL PRODUCTS,2006,69(11):1531_1538. |
| APA | Yang, HJ,Li, BG,Cai, XH,Qi, HY,Luo, YG,&Zhang, GL.(2006).Chiral decalins: Preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox.JOURNAL OF NATURAL PRODUCTS,69(11),1531_1538. |
| MLA | Yang, HJ,et al."Chiral decalins: Preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox".JOURNAL OF NATURAL PRODUCTS 69.11(2006):1531_1538. |
入库方式： OAI收割
来源：成都生物研究所
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