凋亡素A的全合成。
Total synthesis of apoptolidin A.
作者信息
Crimmins Michael T, Christie Hamish S, Long Alan, Chaudhary Kleem
机构信息
Venable and Kenan Laboratories of Chemistry, Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
出版信息
Org Lett. 2009 Feb 19;11(4):831-4. doi: 10.1021/ol802829n.
Abstract
A highly convergent, enantioselective total synthesis of the potent antitumor agent apoptolidin A has been completed. The key transformations include highly selective glycosylations to attach the C27 disaccharide and the C9 6'-deoxy-l-glucose, a cross-metathesis to incorporate the C1-C10 trienoate unit, and a Yamaguchi macrolactonization to complete the macrocycle. Twelve stereocenters in the polypropionate segments and sugar units were established through diastereoselective chlorotitanium enolate aldol reactions.
摘要
高效抗肿瘤药物凋亡诱导素A的高收敛性对映选择性全合成已完成。关键转化步骤包括用于连接C27二糖和C9 6'-脱氧-L-葡萄糖的高选择性糖基化反应、用于引入C1-C10三烯酸酯单元的交叉复分解反应以及用于完成大环结构的山口大环内酯化反应。通过非对映选择性氯钛酸烯醇酯羟醛缩合反应构建了聚丙酸酯片段和糖单元中的12个立体中心。
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本文引用的文献
1
Synthesis of Apoptolidinone.阿朴托利定酮的合成
Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2063-2066. doi: 10.1002/1521-3773(20010601)40:11<2063::AID-ANIE2063>3.0.CO;2-#.
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Total Synthesis of Apoptolidin: Part 2. Coupling of Key Building Blocks and Completion of the Synthesis.凋亡诱导素的全合成：第2部分。关键结构单元的偶联及合成的完成。
Angew Chem Int Ed Engl. 2001 Oct 15;40(20):3854-3857. doi: 10.1002/1521-3773(20011015)40:20<3854::AID-ANIE3854>3.0.CO;2-D.
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Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D.凋亡内酯A和D的合成及其细胞毒性评估
J Org Chem. 2008 Jul 4;73(13):4949-55. doi: 10.1021/jo800545r. Epub 2008 Jun 11.
4
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J Org Chem. 2008 Feb 1;73(3):1036-9. doi: 10.1021/jo7022526. Epub 2007 Dec 29.
5
Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment.凋亡素A的合成研究。1. C(1)-C(11)片段的合成。
J Org Chem. 2008 Feb 1;73(3):1031-5. doi: 10.1021/jo702250z. Epub 2007 Dec 29.
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Short synthesis of the C16-C28 polyketide fragment of apoptolidin A aglycone.凋亡诱导素A苷元C16 - C28聚酮片段的短合成。
Chem Commun (Camb). 2007 Jun 21(23):2411-3. doi: 10.1039/b701293d.
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Isolation, structure determination, and anti-cancer activity of apoptolidin D.凋亡素D的分离、结构测定及抗癌活性
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8
Apoptolidin A: total synthesis and partially glycosylated analogues.阿波托利定A：全合成及部分糖基化类似物
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9
Apoptolidinone A: synthesis of the apoptolidin A aglycone.凋亡内酯A：凋亡内酯A苷元的合成。
Chemistry. 2006 Sep 25;12(28):7364-77. doi: 10.1002/chem.200600461.
10
Apoptolidin: induction of apoptosis by a natural product.阿朴托利定：一种天然产物诱导的细胞凋亡
Angew Chem Int Ed Engl. 2006 Jan 30;45(6):872-93. doi: 10.1002/anie.200502698.
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