Literature DB >> 16597113

Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl- 17-norcharaciol.

Hannes Helmboldt1, Daniel Köhler, Martin Hiersemann.   

Abstract

[reaction: see text] A scalable enantioselective synthesis of the nonnatural 17-norjatrophane diterpene 3-propionyl-15-acetyl-17-norcharaciol is described. Key C/C-connecting transformations are an Evans aldol reaction, an intramolecular carbonyl ene reaction, a Horner-Wadsworth-Emmons olefination, and a ring-closing metathesis for the formation of a 12-membered carbacycle.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 16597113     DOI： 10.1021/ol060115t

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


  13 in total

1.  Crystal structure of rac-(3aR,4S,5aR,6S,9R,10aS,10bR)-3a,5a,9-tri-methyl-tetra-deca-hydro-6,9-ep-oxy-cyclo-hepta-[e]inden-4-ol monohydrate.

Authors:  Andreas Schäfer; Christopher Golz; Hans Preut; Carsten Strohmann; Martin Hiersemann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-08-29

2.  A general enantioselective route to the chamigrene natural product family.

Authors:  David E White; Ian C Stewart; Brinton A Seashore-Ludlow; Robert H Grubbs; Brian M Stoltz
Journal:  Tetrahedron       Date:  2010-03-26       Impact factor: 2.457

3.  Total synthesis of dolabelide C: a phosphate-mediated approach.

Authors:  Paul R Hanson; Rambabu Chegondi; John Nguyen; Christopher D Thomas; Joshua D Waetzig; Alan Whitehead
Journal:  J Org Chem       Date:  2011-04-29       Impact factor: 4.354

4.  A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

Authors:  Joshua D Waetzig; Paul R Hanson
Journal:  Org Lett       Date:  2007-12-07       Impact factor: 6.005

5.  1-Phenyl-5-{[2-(trimethyl-sil-yl)eth-yl]sulfon-yl}-1H-tetra-zole.

Authors:  David Tymann; Björn Nelson; Carsten Strohmann; Hans Preut; Martin Hiersemann
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-17

6.  Crystal structure of (E)-N'-{[(1R,3R)-3-isopropyl-1-methyl-2-oxo-cyclo-pent-yl]methyl-idene}-4-methyl-benzene-sulfono-hydrazide.

Authors:  David Tymann; Dina Christina Dragon; Christopher Golz; Hans Preut; Carsten Strohmann; Martin Hiersemann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-10

7.  Crystal structure of N'-[(E)-(1S,3R)-(3-isopropyl-1-methyl-2-oxo-cyclo-pent-yl)methyl-idene]-4-methyl-benzene-sulfono-hydrazide.

Authors:  David Tymann; Dina Christina Dragon; Christopher Golz; Hans Preut; Carsten Strohmann; Martin Hiersemann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-11-04

8.  Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction.

Authors:  Rita Fürst; Christoph Lentsch; Uwe Rinner
Journal:  European J Org Chem       Date:  2013-03-07

9.  Synthesis of an advanced intermediate of the jatrophane diterpene Pl-4: a dibromide coupling approach.

Authors:  Rita Fürst; Uwe Rinner
Journal:  J Org Chem       Date:  2013-08-13       Impact factor: 4.354

10.  Highly stereoselective synthesis of cyclopentanes bearing four stereocentres by a rhodium carbene-initiated domino sequence.

Authors:  Brendan T Parr; Huw M L Davies
Journal:  Nat Commun       Date:  2014-08-01       Impact factor: 14.919
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.