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一种用于合成1,5-顺式-(E)-二醇的双烯丙基硼化试剂的开发：应用于四纤维蛋白C(23)-C(40)片段的合成。

Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

作者信息

Nuhant Philippe, Kister Jeremy, Lira Ricardo, Sorg Achim, Roush William R

机构信息

Departments of Chemistry, The Scripps Research Institute, Florida, 130 Scripps Way, Jupiter, FL 33458, USA.

出版信息

Tetrahedron. 2011 Sep 2;67(35):6497-6512. doi: 10.1016/j.tet.2011.06.008.

DOI:10.1016/j.tet.2011.06.008
PMID:21857752
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3156408/
Abstract

Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42 and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% e.e.), diastereoselectivity (d.r. >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.

摘要

对纤维四糖素C(23)-C(40)片段2合成的兴趣促使我们开发一种合成1,5-顺式-(E)-二醇的新方法。为此，研究了用索德奎斯特硼烷25R对丙二烯6、33、对映-39、42和45进行动力学控制的硼氢化反应。四丁基铵烯丙基三氟硼酸盐45给出了更好的结果，并用于与两种不同的醛进行双烯丙基硼化反应序列，以通常高的产率(72-98%)、高对映选择性(>95% ee)、非对映选择性(d.r.>20:1)和(E)/(Z)选择性(>20:1)提供目标1,5-顺式-(E)-二醇。这种新方法被应用于纤维四糖素C(23)-C(40)片段2的合成。

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2
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Org Lett. 2011 May 6;13(9):2484-7. doi: 10.1021/ol200735r. Epub 2011 Apr 6.
3
Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.对映选择性和非对映选择性合成（E）-1,5-顺式二醇：在四纤维菌素 C(23)-C(40)片段合成中的应用。
Org Lett. 2011 Apr 1;13(7):1868-71. doi: 10.1021/ol2003836. Epub 2011 Mar 4.
4
Versatile configuration-encoded strategy for rapid synthesis of 1,5-polyol stereoisomers.多功能构象编码策略用于快速合成 1,5-聚醇立体异构体。
Org Lett. 2010 Nov 5;12(21):5016-9. doi: 10.1021/ol1021417.
5
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Synlett. 2010 Mar 1;2010(4):667-674. doi: 10.1055/s-0029-1219376.
6
SULFANYLATION OF 1,3-DITHIANE ANIONS BY 5-(ALKYLSULFANYL)-1-PHENYLTETRAZOLES.5-（烷基硫烷基）-1-苯基四氮唑对1,3-二噻烷阴离子的硫烷基化反应
Collect Czechoslov Chem Commun. 2009 Jun 1;74(5):7711-7783. doi: 10.1135/cccc2008195.
7
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8
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Org Lett. 2009 Dec 3;11(23):5538-41. doi: 10.1021/ol902364d.
9
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10
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J Am Chem Soc. 2009 Oct 14;131(40):14174-5. doi: 10.1021/ja905494c.