Literature DB >> 24098237

rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis-(acet-yloxy)-3-oxo-2-phenyl-octa-hydro-1H-iso-indole-4-carboxyl-ate.

Flavien A A Toze1, Eugeniya V Nikitina, Vladimir P Zaytsev, Fedor I Zubkov, Victor N Khrustalev.   

Abstract

The title molecule, C20H23NO7, the product of nucleophilic cleavage of the 3a,6-ep-oxy bridge in 1-oxo-2-phenyl-octa-hydro-3a,6-ep-oxy-iso-indole-7-carboxyl-ate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxyl-ate substituent as the flap) and a cyclo-hexane ring in a chair conformation. The carboxyl-ate substituent occupies the equatorial position, whereas the two acet-yloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3 (3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98 (6)°. In the crystal, mol-ecules are linked into zigzag chains along the c-axis direction by C-H⋯O hydrogen bonds.

Entities:  

Year:  2013        PMID: 24098237      PMCID: PMC3790418          DOI: 10.1107/S1600536813025129

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


  3 in total

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Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates.

Authors:  Diederica D Claeys; Christian V Stevens; Bart I Roman; Pieter Van De Caveye; Michel Waroquier; Veronique Van Speybroeck
Journal:  Org Biomol Chem       Date:  2010-06-11       Impact factor: 3.876

3.  Remodelling of the natural product fumagillol employing a reaction discovery approach.

Authors:  Bradley R Balthaser; Meghan C Maloney; Aaron B Beeler; John A Porco; John K Snyder
Journal:  Nat Chem       Date:  2011-12       Impact factor: 24.427

  3 in total

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