Literature DB >> 28686815

Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Tyler M Rohrs1, Qi Qin1, Paul E Floreancig1.   

Abstract

Re2 O7 catalysis effects efficient and stereoselective dehydrative cyclization reactions from monoallylic diols, with stereocontrol arising from thermodynamic equilibration. This method was applied to a rapid synthesis of the spliceosome inhibitor herboxidiene. The route was also utilized for the synthesis of an analogue that highlights the importance of a single methyl group in biasing the conformation in the acyclic region of the molecule.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  conformational analysis; cyclization; natural products; oxygen heterocycles; solvolysis

Mesh：

Substances：

Year:  2017        PMID： 28686815      PMCID： PMC5687070          DOI： 10.1002/anie.201705924

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  51 in total

1.  Identification of SAP155 as the target of GEX1A (Herboxidiene), an antitumor natural product.

Authors:  Makoto Hasegawa; Tatsuhiro Miura; Kouji Kuzuya; Ayu Inoue; Se Won Ki; Sueharu Horinouchi; Tetsuo Yoshida; Tatsuki Kunoh; Koichi Koseki; Koshiki Mino; Ryuzo Sasaki; Minoru Yoshida; Tamio Mizukami
Journal:  ACS Chem Biol       Date:  2011-01-13       Impact factor: 5.100

2.  FeCl(3)-Catalyzed highly diastereoselective synthesis of substituted piperidines and tetrahydropyrans.

Authors:  Amandine Guérinot; Anna Serra-Muns; Christian Gnamm; Charlélie Bensoussan; Sébastien Reymond; Janine Cossy
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  Total synthesis of (-)-laulimalide: Pd-catalyzed stereospecific ring construction of the substituted 3,6-dihydro[2H]pyran units.

Authors:  Jun'ichi Uenishi; Masashi Ohmi
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-29       Impact factor: 15.336

4.  Boronic acid catalysis as a mild and versatile strategy for direct carbo- and heterocyclizations of free allylic alcohols.

Authors:  Hongchao Zheng; Sina Ghanbari; Shinji Nakamura; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-15       Impact factor: 15.336

Review 5.  Profound methyl effects in drug discovery and a call for new C-H methylation reactions.

Authors:  Heike Schönherr; Tim Cernak
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-22       Impact factor: 15.336

Review 6.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

7.  A chiral bidentate sp2-N ligand, Naph-diPIM: application to CpRu-catalyzed asymmetric dehydrative C-, N-, and O-allylation.

Authors:  Kengo Miyata; Hironori Kutsuna; Sho Kawakami; Masato Kitamura
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-15       Impact factor: 15.336

8.  Au-catalyzed cyclization of monoallylic diols.

Authors:  Aaron Aponick; Chuan-Ying Li; Berenger Biannic
Journal:  Org Lett       Date:  2008-01-25       Impact factor: 6.005

9.  Herboxidiene, a new herbicidal substance from Streptomyces chromofuscus A7847. Taxonomy, fermentation, isolation, physico-chemical and biological properties.

Authors:  M Miller-Wideman; N Makkar; M Tran; B Isaac; N Biest; R Stonard
Journal:  J Antibiot (Tokyo)       Date:  1992-06       Impact factor: 2.649

10.  The importance of hydrogen bonding to stereoselectivity and catalyst turnover in gold-catalyzed cyclization of monoallylic diols.

Authors:  Thomas Ghebreghiorgis; Berenger Biannic; Brian H Kirk; Daniel H Ess; Aaron Aponick
Journal:  J Am Chem Soc       Date:  2012-09-20       Impact factor: 15.419
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  1 in total

1.  GEX1A, a Polyketide from Streptomyces chromofuscus, Corrects the Cellular Defects Associated with Niemann-Pick Type C1 in Human Fibroblasts.

Authors:  Eve A Granatosky; Nina DiPrimio; Jarred R E Pickering; D Cole Stevens; Ethan O Perlstein; Richard E Taylor
Journal:  J Nat Prod       Date:  2018-09-06       Impact factor: 4.050
  1 in total

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