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Depurinating acylfulvene-DNA adducts: characterizing cellular chemical reactions of a selective antitumor agent.脱嘌呤酰基富烯-DNA加合物：表征一种选择性抗肿瘤剂的细胞化学反应
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（-）-酰基富烯和（-）-irofulven 的对映选择性全合成。

Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

J Org Chem. 2009 Dec 18;74(24):9292-304. doi: 10.1021/jo901926z.

DOI:10.1021/jo901926z
PMID:19938810
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2805080/
Abstract

We report our full account of the enantioselective total synthesis of (-)-acylfulvene (1) and (-)-irofulven (2), which features metathesis reactions for the rapid assembly of the molecular framework of these antitumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketenethioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent IPNBSH for a late-stage reductive allylic transposition reaction, and (4) the final RCM/dehydrogenation sequence for the formation of (-)-acylfulvene (1) and (-)-irofulven (2).

摘要

我们报告了 (-)-酰基fulvene (1) 和 (-)-irofulven (2) 的对映选择性全合成的完整描述，该合成采用了复分解反应，快速构建了这些抗肿瘤药物的分子骨架。我们讨论了：（1）使用应变环丙基酮硫缩醛的 Evans Cu 催化的Aldol 加成反应的应用；（2）在具有挑战性的条件下高效的烯炔环 closing metathesis 级联反应；（3）试剂 IPNBSH 用于晚期还原烯丙基反式置换反应；（4）(-)-酰基 fulvene (1) 和 (-)-irofulven (2) 的最终 RCM/脱氢序列的形成。