通过溴鎓离子引发的环氧开环串联反应全合成对映-二氧杂环庚烷脱氢紫衫叶素。
Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade.
作者信息
Tanuwidjaja Jessica, Ng Sze-Sze, Jamison Timothy F
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
出版信息
J Am Chem Soc. 2009 Sep 2;131(34):12084-5. doi: 10.1021/ja9052366.
Abstract
In the first total synthesis of ent-dioxepandehydrothyrsiferol, the signature trans-anti-trans 7,7,6-fused tricyclic polyether framework was constructed in a single bromonium-initiated epoxide-opening cascade that incorporates both endo- and exo-selective epoxide openings, each directed by the substitution pattern of the epoxide (methyl groups). This study thus demonstrates the feasibility of a possible biogenesis.
摘要
在对映-二氧杂环庚烷脱氢紫衫叶酚的首次全合成中，标志性的反式-反式-反式7,7,6-稠合三环聚醚骨架是在一个由溴鎓引发的环氧开环串联反应中构建而成的，该反应包含内型和外型选择性环氧开环，每种开环都由环氧（甲基）的取代模式引导。因此，这项研究证明了一种可能生物合成途径的可行性。
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2
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