Literature DB >> 18998640

Synthesis and structure revision of nakiterpiosin.

Shuanhu Gao1, Qiaoling Wang, Chuo Chen.   

Abstract

This manuscript describes a convergent synthesis and the revision of the relative stereochemistry of nakiterpiosin, a marine C-nor-D-homosteroid. Our synthesis features a late-stage carbonylative Stille cross-coupling reaction and a photo-Nazarov cyclization reaction that deliver the complete nakiterpiosin skeleton efficiently.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 18998640      PMCID： PMC2635422          DOI： 10.1021/ja808110d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  33 in total

Review 1.  The Hedgehog response network: sensors, switches, and routers.

Authors:  Lawrence Lum; Philip A Beachy
Journal:  Science       Date:  2004-06-18       Impact factor: 47.728

2.  Accelerated asymmetric transfer hydrogenation of aromatic ketones in water.

Authors:  Xiaofeng Wu; Xiaoguang Li; William Hems; Frank King; Jianliang Xiao
Journal:  Org Biomol Chem       Date:  2004-05-25       Impact factor: 3.876

Review 3.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

Review 4.  Nature's inventory of halogenation catalysts: oxidative strategies predominate.

Authors:  Frédéric H Vaillancourt; Ellen Yeh; David A Vosburg; Sylvie Garneau-Tsodikova; Christopher T Walsh
Journal:  Chem Rev       Date:  2006-08       Impact factor: 60.622

5.  Teratological research at the USDA-ARS poisonous plant research laboratory.

Authors:  L F James
Journal:  J Nat Toxins       Date:  1999-02

6.  A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents.

Authors:  Alberto Spaggiari; Daniele Vaccari; Paolo Davoli; Giovanni Torre; Fabio Prati
Journal:  J Org Chem       Date:  2007-02-13       Impact factor: 4.354

7.  Polarizing the Nazarov cyclization: the impact of dienone substitution pattern on reactivity and selectivity.

Authors:  Wei He; Ildiko R Herrick; Tulay A Atesin; Patrick A Caruana; Colleen A Kellenberger; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

Review 8.  Hedgehog signaling in development and homeostasis of the gastrointestinal tract.

Authors:  Gijs R van den Brink
Journal:  Physiol Rev       Date:  2007-10       Impact factor: 37.312

9.  Rh III- and Ir III-catalyzed asymmetric transfer hydrogenation of ketones in water.

Authors:  Xiaofeng Wu; Xiaohong Li; Antonio Zanotti-Gerosa; Allan Pettman; Jianke Liu; Allan James Mills; Jianliang Xiao
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  A paracrine requirement for hedgehog signalling in cancer.

Authors:  Robert L Yauch; Stephen E Gould; Suzie J Scales; Tracy Tang; Hua Tian; Christina P Ahn; Derek Marshall; Ling Fu; Thomas Januario; Dara Kallop; Michelle Nannini-Pepe; Karen Kotkow; James C Marsters; Lee L Rubin; Frederic J de Sauvage
Journal:  Nature       Date:  2008-08-27       Impact factor: 49.962
View more
  14 in total

1.  Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt.

Authors:  Ravi P Singh; Bruce M Foxman; Li Deng
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419

Review 2.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

3.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

4.  Asymmetric Nazarov Cyclizations.

Authors:  Naoyuki Shimada; Craig Stewart; Marcus A Tius
Journal:  Tetrahedron       Date:  2011-08-19       Impact factor: 2.457

5.  Chemical and biological studies of nakiterpiosin and nakiterpiosinone.

Authors:  Shuanhu Gao; Qiaoling Wang; Lily Jun-Shen Huang; Lawrence Lum; Chuo Chen
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419

6.  The Chemistry and Biology of Nakiterpiosin - C-nor-D-Homosteroids.

Authors:  Shuanhu Gao; Qiaoling Wang; Gelin Wang; Brett Lomenick; Jie Liu; Chih-Wei Fan; Lih-Wen Deng; Jing Huang; Lawrence Lum; Chuo Chen
Journal:  Synlett       Date:  2012-10       Impact factor: 2.454

7.  Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.

Authors:  Xiaocong Xie; Yi Li; Joseph M Fox
Journal:  Org Lett       Date:  2013-03-20       Impact factor: 6.005

8.  Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.

Authors:  Ji-Bao Xia; Chen Zhu; Chuo Chen
Journal:  J Am Chem Soc       Date:  2013-11-12       Impact factor: 15.419

9.  Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

Authors:  William F Bow; Ashok K Basak; Anais Jolit; David A Vicic; Marcus A Tius
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

10.  Exploratory research on bioactive natural products with a focus on biological phenomena.

Authors:  Daisuke Uemura
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.