| Construction of the Core of Pseudolaric Acid A and Mechanistic Studies on Intramolecular [4+3] Cycloaddition |
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| 引用本文： | Xun Tian JIANG,Li Gong OU,Dong Mei HAN,Yu Feng ZHAI,Dong Lu BAI* Shanghai Institute of Materia Medica,Chinese Academy of Sciences,294 Taiyuan Road,Shanghai,200031. Construction of the Core of Pseudolaric Acid A and Mechanistic Studies on Intramolecular [4+3] Cycloaddition[J]. 中国化学快报, 2001, 0(2) |
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| 作者姓名： | Xun Tian JIANG Li Gong OU Dong Mei HAN Yu Feng ZHAI Dong Lu BAI* Shanghai Institute of Materia Medica Chinese Academy of Sciences 294 Taiyuan Road Shanghai 200031 |
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| 作者单位： | Xun Tian JIANG，Li Gong OU，Dong Mei HAN，Yu Feng ZHAI，Dong Lu BAI* Shanghai Institute of Materia Medica，Chinese Academy of Sciences，294 Taiyuan Road，Shanghai，200031 |
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| 基金项目： | the National Natural Science Foundation of China. |
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| 摘 要： | Pseudolaric acid A (1), which exhibits antifungal activity, cytotoxicity against several tumor cell lines in vitro, as well as contraceptive effects in mice, is a diterpenoid compound isolated from Pseudolarix Kaemferi1. The unusual structural feature in this molecule is a trans arrangement of the lactone and acetoxy group at the fused junction of 5, 7-fused ring skeleton bearing four contiguous stereogenic centers. The synthetic challenges posed by these structural elements in a rather compa…
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Construction of the Core of Pseudolaric Acid A and Mechanistic Studies on Intramolecular [4+3] Cycloaddition |
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| Xun Tian JIANG,Li Gong OU,Dong Mei HAN,Yu Feng ZHAI,Dong Lu BAI. Construction of the Core of Pseudolaric Acid A and Mechanistic Studies on Intramolecular [4+3] Cycloaddition[J]. Chinese Chemical Letters, 2001, 0(2) |
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| Authors: | Xun Tian JIANG Li Gong OU Dong Mei HAN Yu Feng ZHAI Dong Lu BAI |
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| Affiliation: | Xun Tian JIANG,Li Gong OU,Dong Mei HAN,Yu Feng ZHAI,Dong Lu BAI* Shanghai Institute of Materia Medica,Chinese Academy of Sciences,294 Taiyuan Road,Shanghai,200031 |
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| Abstract: | This paper describes the construction of hemiacetal 2, the core of pseudolaric acid A via oxidative cleavage of acetonide 6 or 7 and enolization-hemiacetalization of aldehyde 8. A plausible general mechanism for the intramolecular [4+3] cycloaddition of sulfoxide 4 to adduct 3 is suggested. |
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| Keywords: | Pseudolaric acid A 5 7- membered fused ring hemiacetal intramolecular [4+3] cycloaddition mechanism. |
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