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莱康那定类化合物：（+）-莱康那定A和（-）-莱康那定B的对映选择性全合成

The lyconadins: enantioselective total syntheses of (+)-lyconadin A and (-)-lyconadin B.

作者信息

Beshore Douglas C, Smith Amos B

机构信息

Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.

出版信息

J Am Chem Soc. 2008 Oct 15;130(41):13778-89. doi: 10.1021/ja804939r. Epub 2008 Sep 18.

DOI:10.1021/ja804939r
PMID:18798629
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2819465/
Abstract

A full account of the enantioselective total syntheses of (+)-lyconadin A (1) and (-)-lyconadin B (2) is presented. Central to this venture was recognition and deployment of a key strategy-level intramolecular aldol/conjugate addition cascade that led, in a single operation, to two new carbon-carbon sigma-bonds, three new stereogenic centers, and two new rings, albeit with the incorrect stereogenicity at C(12) for the lyconadins. Correction of the C(12) stereogenicity was achieved via innovative use of a protonated intramolecular aminal. An aminoiodo olefin cyclization, in conjunction with alpha-pyridinone and 3,4-dihydropyridinone annulation protocols, permitted completion of the syntheses of (+)-lyconadin A (1) and (-)-lyconadin B (2), respectively.

摘要

本文详细介绍了(+)-lyconadin A（1）和(-)-lyconadin B（2）的对映选择性全合成。这一研究的核心是识别并运用一种关键的策略级分子内羟醛/共轭加成串联反应，该反应在一次操作中形成了两个新的碳-碳σ键、三个新的立体中心和两个新的环，尽管lyconadins在C(12)处的立体化学构型不正确。通过创新性地使用质子化分子内亚胺，实现了C(12)立体化学构型的校正。氨基碘代烯烃环化反应与α-吡啶酮和3,4-二氢吡啶酮环合方案相结合，分别完成了(+)-lyconadin A（1）和(-)-lyconadin B（2）的合成。

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2
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3
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Org Lett. 2007 Jul 5;9(14):2633-6. doi: 10.1021/ol070770g. Epub 2007 Jun 6.
4
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J Am Chem Soc. 2007 Apr 11;129(14):4148-9. doi: 10.1021/ja070336+. Epub 2007 Mar 17.
5
Lycopladines B-D and lyconadin B, new alkaloids from Lycopodium complanatum.
Bioorg Med Chem. 2006 Sep 1;14(17):5995-6000. doi: 10.1016/j.bmc.2006.05.028. Epub 2006 Jun 5.
6
Stereoselective cascade reactions that incorporate a 7-exo acyl radical cyclization.
Org Lett. 2006 Apr 27;8(9):1867-70. doi: 10.1021/ol0604264.
7
The Lycopodium alkaloids.
Alkaloids Chem Biol. 2005;61:1-57. doi: 10.1016/s1099-4831(05)61001-2.
8
The Lycopodium alkaloids.
Nat Prod Rep. 2004 Dec;21(6):752-72. doi: 10.1039/b409720n. Epub 2004 Oct 21.
9
Generation and trapping of alkene radical cations under nonoxidizing conditions: formation of six-membered rings by exo- and endo-mode cyclizations.
Org Lett. 2002 Jul 25;4(15):2573-5. doi: 10.1021/ol026204x.
10
Azatriquinanes: Synthesis, Structure, and Reactivity.
J Org Chem. 1998 Aug 21;63(17):6016-6020. doi: 10.1021/jo980788s.

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