一种用于吡咯并咪唑醌生物碱合成的便捷碳-氢官能化平台。
A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis.
作者信息
Smith Myles W, Falk Isaac D, Ikemoto Hideya, Burns Noah Z
机构信息
Department of Chemistry, Stanford University, Stanford, California 94305, United States.
出版信息
Tetrahedron. 2019 Jun 14;75(24):3366-3370. doi: 10.1016/j.tet.2019.05.009. Epub 2019 May 8.
Abstract
Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family - and in particular the antitumor discorhabdins - built upon sequential selective C-H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A-C, makaluvamines D and I, and discorhadbin E. Additionally, we describe efforts to develop the first catalytic asymmetric entry to the discorhabdin subclass.
摘要
吡咯并咪唑醌生物碱是一类结构引人入胜的天然产物，具有一系列有用的生物学特性。在此，我们基于色胺的顺序选择性C-H官能化，提出了一个通用且可扩展的平台，用于合成这个多样化的家族，特别是抗肿瘤的盘状海绵素。通过对达米罗宁A-C、马卡鲁胺D和I以及盘状海绵素E的简短形式合成，展示了该策略的实用性。此外，我们还描述了开发盘状海绵素亚类首个催化不对称合成方法的努力。
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本文引用的文献
1
Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.
J Am Chem Soc. 2018 Nov 21;140(46):15646-15650. doi: 10.1021/jacs.8b10799. Epub 2018 Nov 12.
2
Catalytic Enantioselective Dihalogenation in Total Synthesis.
Acc Chem Res. 2018 May 15;51(5):1260-1271. doi: 10.1021/acs.accounts.8b00064. Epub 2018 Apr 17.
3
Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters.
J Am Chem Soc. 2017 Sep 27;139(38):13414-13419. doi: 10.1021/jacs.7b06029. Epub 2017 Sep 15.
4
Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid.
J Am Chem Soc. 2016 Dec 14;138(49):15845-15848. doi: 10.1021/jacs.6b10706. Epub 2016 Nov 29.
5
Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols.
J Am Chem Soc. 2015 Mar 25;137(11):3795-8. doi: 10.1021/jacs.5b01384. Epub 2015 Mar 10.
6
C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.
J Org Chem. 2014 Nov 21;79(22):11254-63. doi: 10.1021/jo502062z. Epub 2014 Nov 10.
7
Catalytic enantioselective dibromination of allylic alcohols.
J Am Chem Soc. 2013 Sep 4;135(35):12960-3. doi: 10.1021/ja4083182. Epub 2013 Aug 21.
8
Chiral N,N'-dioxides: new ligands and organocatalysts for catalytic asymmetric reactions.
Acc Chem Res. 2011 Aug 16;44(8):574-87. doi: 10.1021/ar200015s. Epub 2011 Jun 24.
9
Discorhabdins and pyrroloiminoquinone-related alkaloids.
Chem Rev. 2011 Sep 14;111(9):5465-91. doi: 10.1021/cr100435g. Epub 2011 Jun 21.
10
The synthetic and biological studies of discorhabdins and related compounds.
Org Biomol Chem. 2011 Jul 7;9(13):4959-76. doi: 10.1039/c1ob05058c. Epub 2011 May 20.
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