Literature DB >> 23763296

Stereoselective synthesis of dienyl-carboxylate building blocks: formal synthesis of inthomycin C.

Caroline Souris1, Frédéric Frébault, Ashay Patel, Davide Audisio, K N Houk, Nuno Maulide.   

Abstract

A direct synthesis of stereodefined halodienes is reported. Those key building blocks enable a concise access to polyenic products, as demonstrated in a modular synthesis of Inthomycin C.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23763296      PMCID： PMC3739699          DOI： 10.1021/ol401226y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

1.  cis-3,4-Dichlorocyclobutene as a Versatile Synthon in Organic Synthesis. Rapid Entry into Complex Polycyclic Systems with Remarkably Stereospecific Reactions We thank Drs. D. H. Huang and G. Siuzdak for their assistance with NMR spectroscopy and mass spectrometry, respectively. This work was financially supported by the National Institutes of Health (USA) and The Skaggs Institute for Chemical Biology, a postdoctoral fellowship from the Skaggs Institute for Research (to V.G.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

Authors:  K. C. Nicolaou; Juan A. Vega; Georgios Vassilikogiannakis
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-03       Impact factor: 15.336

2.  Total synthesis of (-)-dictyostatin.

Authors:  Gregory W O'Neil; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

3.  Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling.

Authors:  Suk Joong Lee; Kaitlyn C Gray; James S Paek; Martin D Burke
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

4.  Stereoretentive Suzuki-Miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-peridinin.

Authors:  Eric M Woerly; Alan H Cherney; Erin K Davis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

5.  The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst.

Authors:  Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

6.  Concise total synthesis of (-)-myxalamide A.

Authors:  Kazuhiro Fujita; Ryosuke Matsui; Takahiro Suzuki; Susumu Kobayashi
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-13       Impact factor: 15.336

7.  (Z)-(2-bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.

Authors:  Eric M Woerly; Justin R Struble; Nagarjuna Palyam; Sean P O'Hara; Martin D Burke
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

8.  Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents.

Authors:  Massimo Giannerini; Martín Fañanás-Mastral; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2012-02-27       Impact factor: 15.419

9.  Altering the allowed/forbidden gap in cyclobutene electrocyclic reactions: experimental and theoretical evaluations of the effect of planarity constraints.

Authors:  Patrick S Lee; Shogo Sakai; Peter Hörstermann; Wolfgang R Roth; E Adam Kallel; K N Houk
Journal:  J Am Chem Soc       Date:  2003-05-14       Impact factor: 15.419

10.  A powerful chiral counteranion motif for asymmetric catalysis.

Authors:  Pilar García-García; Frank Lay; Patricia García-García; Constantinos Rabalakos; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
View more
  7 in total

1.  Production and Identification of Inthomycin B Produced by a Deep-Sea Sediment-Derived Streptomyces sp. YB104 Based on Cultivation-Dependent Approach.

Authors:  Qihao Wu; Gaiyun Zhang; Bixia Wang; Xin Li; Shaopeng Yue; Jianwei Chen; Huawei Zhang; Hong Wang
Journal:  Curr Microbiol       Date:  2018-03-08       Impact factor: 2.188

2.  Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization.

Authors:  Sepand K Nistanaki; Hosea M Nelson
Journal:  ACS Macro Lett       Date:  2020-05-01       Impact factor: 6.903

3.  Dynamic behaviour of monohaptoallylpalladium species: internal coordination as a driving force in allylic alkylation chemistry.

Authors:  Lan-Gui Xie; Viktor Bagutski; Davide Audisio; Larry M Wolf; Volker Schmidts; Kathrin Hofmann; Cornelia Wirtz; Walter Thiel; Christina M Thiele; Nuno Maulide
Journal:  Chem Sci       Date:  2015-07-06       Impact factor: 9.825

4.  Towards a Scalable Synthesis of 2-Oxabicyclo[2.2.0]hex-5-en-3-one Using Flow Photochemistry.

Authors:  Jason D Williams; Yuma Otake; Guilhem Coussanes; Iakovos Saridakis; Nuno Maulide; C Oliver Kappe
Journal:  ChemPhotoChem       Date:  2019-02-18

Review 5.  Progress in the total synthesis of inthomycins.

Authors:  Bidyut Kumar Senapati
Journal:  Beilstein J Org Chem       Date:  2021-01-07       Impact factor: 2.883

6.  Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.

Authors:  Mingyue Wu; Zhaobin Han; Huanzhen Ni; Nengzhong Wang; Kuiling Ding; Yixin Lu
Journal:  Chem Sci       Date:  2022-02-11       Impact factor: 9.825

7.  Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions.

Authors:  Eskedar Tessema; Vijayanath Elakkat; Chiao-Fan Chiu; Zong-Lin Tsai; Ka Long Chan; Chia-Rui Shen; Han-Chang Su; Norman Lu
Journal:  Molecules       Date:  2021-03-05       Impact factor: 4.411
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.