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| DOI | 10.1126/science.aay9173 |
| Total synthesis of the complex taxane diterpene canataxpropellane | |
| Schneider F.; Samarin K.; Zanella S.; Gaich T. | |
| 发表日期 | 2020 |
| ISSN | 0036-8075 |
| 起始页码 | 676 |
| 结束页码 | 681 |
| 卷号 | 367期号:6478 |
| 英文摘要 | Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C–C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (–)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (–)-canataxpropellane (2) was assembled in two steps using a Diels–Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the Diels–Alder reaction. © 2020 American Association for the Advancement of Science. All rights reserved. |
| 关键词 | canataxpropellanediterpenoidsiloxanetaxane derivativeunclassified drugcancerchemical analysischemical bondingdisease treatmentmedicineterpeneArticlechiralitycycloadditionDiels Alder reactiondrug structuredrug synthesisenantioselectivityphotooxidationpriority journalstereoselectivityAlnus |
| 语种 | 英语 |
| 来源机构 | Science |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://gcip.llas.ac.cn/handle/2XKMVOVA/133741 |
| 推荐引用方式 GB/T 7714 | Schneider F.,Samarin K.,Zanella S.,et al. Total synthesis of the complex taxane diterpene canataxpropellane[J]. Science,2020,367(6478). |
| APA | Schneider F.,Samarin K.,Zanella S.,&Gaich T..(2020).Total synthesis of the complex taxane diterpene canataxpropellane.,367(6478). |
| MLA | Schneider F.,et al."Total synthesis of the complex taxane diterpene canataxpropellane".367.6478(2020). |
| 条目包含的文件 | 条目无相关文件。 | |||||
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