Literature DB >> 22963036

Oxyanionic sigmatropic rearrangements relevant to cyclooctadienone formation in penostatins I and F.

Matthew J Jansma1, Thomas R Hoye.   

Abstract

The results of several experiments designed to probe the energetic viability of a reaction path for generation of penostatins I (3) and F (4) via spontaneous [3,3]-sigmatropic rearrangement are reported. In particular, the enolate derived from the 2-vinyl-6-acyldihydropyran 8-cis gave cyclooctadienone 12 via facile anionic oxy-Claisen rearrangement, demonstrating the feasibility of such an event.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22963036      PMCID： PMC3501534          DOI： 10.1021/ol3019488

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


  6 in total

1.  Total synthesis of penostatin B.

Authors:  Kosuke Fujioka; Hiromasa Yokoe; Masahiro Yoshida; Kozo Shishido
Journal:  Org Lett       Date:  2011-12-06       Impact factor: 6.005

2.  Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-beta-KDO.

Authors:  S D Burke; G M Sametz
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

3.  Total synthesis of (+/-)-deoxypenostatin A. Approaches to the syntheses of penostatins A and B.

Authors:  B B Snider; T Liu
Journal:  J Org Chem       Date:  2000-12-15       Impact factor: 4.354

4.  Rapid assembly of the bicyclo[5.3.1]undecenone core of penostatin F: a successive Diels-Alder/Claisen reaction strategy with an efficient stereochemical relay.

Authors:  Louis Barriault; Patrick J A Ang; Roch M A Lavigne
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

5.  Rate acceleration of anionic oxy-cope rearrangements induced by an additional unsaturation.

Authors:  Lionel Gentric; Issam Hanna; Alexandre Huboux; Rachida Zaghdoudi
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

6.  Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate.

Authors:  Barry M Trost; Aaron Aponick
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419
  6 in total
  1 in total

1.  Cryptic Biosynthesis of the Berkeleypenostatins from Coculture of Extremophilic Penicillium sp.

Authors:  Andrea A Stierle; Donald B Stierle; Daniel Decato; Jeremy Alverson; Lily Apedaile
Journal:  J Nat Prod       Date:  2021-05-06       Impact factor: 4.050
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.