Literature DB >> 31889735

A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis.

Myles W Smith1, Isaac D Falk1, Hideya Ikemoto1, Noah Z Burns1.   

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.

Entities:  

Year:  2019        PMID: 31889735      PMCID: PMC6937132          DOI: 10.1016/j.tet.2019.05.009

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  21 in total

1.  Catalytic asymmetric bromoamination of chalcones: highly efficient synthesis of chiral alpha-bromo-beta-amino ketone derivatives.

Authors:  Yunfei Cai; Xiaohua Liu; Yonghai Hui; Jun Jiang; Wentao Wang; Weiliang Chen; Lili Lin; Xiaoming Feng
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

2.  Makaluvamines H-M and damirone C from the pohnpeian sponge Zyzzya fuliginosa.

Authors:  E W Schmidt; M K Harper; D J Faulkner
Journal:  J Nat Prod       Date:  1995-12       Impact factor: 4.050

3.  Anti-infective discorhabdins from a deep-water alaskan sponge of the genus Latrunculia.

Authors:  Minkyun Na; Yuanqing Ding; Bin Wang; Babu L Tekwani; Raymond F Schinazi; Scott Franzblau; Michelle Kelly; Robert Stone; Xing-Cong Li; Daneel Ferreira; Mark T Hamann
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

4.  Chiral N,N'-dioxides: new ligands and organocatalysts for catalytic asymmetric reactions.

Authors:  XiaoHua Liu; LiLi Lin; XiaoMing Feng
Journal:  Acc Chem Res       Date:  2011-06-24       Impact factor: 22.384

5.  Catalytic enantioselective dibromination of allylic alcohols.

Authors:  Dennis X Hu; Grant M Shibuya; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2013-08-21       Impact factor: 15.419

6.  A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D.

Authors:  Kelly Marshall Aubart; Clayton H. Heathcock
Journal:  J Org Chem       Date:  1999-01-08       Impact factor: 4.354

7.  The synthetic and biological studies of discorhabdins and related compounds.

Authors:  Yasufumi Wada; Yu Harayama; Daigo Kamimura; Masako Yoshida; Tomoyuki Shibata; Kousaku Fujiwara; Koji Morimoto; Hiromichi Fujioka; Yasuyuki Kita
Journal:  Org Biomol Chem       Date:  2011-05-20       Impact factor: 3.876

8.  The first total synthesis of discorhabdin A.

Authors:  Hirofumi Tohma; Yu Harayama; Miki Hashizume; Minako Iwata; Yorito Kiyono; Masahiro Egi; Yasuyuki Kita
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

9.  Synthesis of tetrahydropyrroloiminoquinone alkaloids based on electrochemically generated hypervalent iodine oxidative cyclization.

Authors:  Keisuke Inoue; Yuichi Ishikawa; Shigeru Nishiyama
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

10.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

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