Literature DB >> 22506757

An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Sudeshna Roy1, Christopher D Spilling.   

Abstract

Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22506757      PMCID： PMC3345562          DOI： 10.1021/ol300597u

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


  20 in total

1.  Total synthesis of (2S,3S,5S,10S)-6,9-epoxynonadec-18-ene-7,10-diol and formal total synthesis of (+)-trans-kumausyne from D-arabinose.

Authors:  R R Gadikota; C S Callam; T L Lowary
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

2.  First total synthesis and structural reassignment of (-)-aplysiallene.

Authors:  Jian Wang; Brian L Pagenkopf
Journal:  Org Lett       Date:  2007-08-11       Impact factor: 6.005

3.  Acid-Mediated Conversion of Methylene-Interrupted Bisepoxides to Tetrahydrofurans: A Biomimetic Transformation.

Authors:  Robert J. Capon; Russell A. Barrow
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

4.  Development of a concise and general enantioselective approach to 2,5-disubstituted-3-hydroxytetrahydrofurans.

Authors:  Baldip Kang; Jeffrey Mowat; Thomas Pinter; Robert Britton
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

5.  A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

Authors:  Peng Jiao; Masanori Kawasaki; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Ring-closing metathesis in the synthesis of BC ring-systems of taxol.

Authors:  Cong Ma; Stéphanie Schiltz; Xavier F Le Goff; Joëlle Prunet
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

7.  Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2010-10-28       Impact factor: 6.005

8.  Stereoselective synthesis of cyclic ethers via the palladium-catalyzed intramolecular addition of alcohols to phosphono allylic carbonates.

Authors:  Anyu He; Nongnuch Sutivisedsak; Christopher D Spilling
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

9.  Total synthesis of (+)-oocydin A: application of the Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl 9-BBN.

Authors:  Emmanuel Roulland
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Highly diastereoselective Katsuki-Jacobsen oxidation-epoxidation of alpha-silyloxy sulfinyl dienes: synthetic applications.

Authors:  Roberto Fernández de la Pradilla; Alejandro Castellanos; Iñaki Osante; Ignacio Colomer; Mateo I Sánchez
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354
View more
  2 in total

1.  Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.

Authors:  Nongnuch Sutivisedsak; Surendra Dawadi; Christopher D Spilling
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Relay cross metathesis reactions of vinylphosphonates.

Authors:  Raj K Malla; Jeremy N Ridenour; Christopher D Spilling
Journal:  Beilstein J Org Chem       Date:  2014-08-19       Impact factor: 2.883
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.