Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 26, 2010
Previous Article Next Article

A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A

Author affiliations

Abstract

A concise, enantioselective synthesis of the Phase I anticancer agent, (−)-salinosporamide A, is described. The brevity of the described strategy stems from a key bis-cyclization of a β-keto tertiary amide, accomplished on gram scale, which retains optical purity enabled by A1,3-strain rendering epimerization slow relative to the rate of bis-cyclization. The versatility of the strategy for derivative synthesis is demonstrated by the synthesis of (−)-homosalinosporamide A.

Graphical abstract: A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Mar 2010, accepted on 22 Apr 2010 and first published on 25 May 2010


Article type: Communication
DOI: 10.1039/C0CC00607F
Citation: Chem. Commun., 2010,46, 4803-4805

  •   Request permissions

    A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A

    H. Nguyen, G. Ma and D. Romo, Chem. Commun., 2010, 46, 4803
    DOI: 10.1039/C0CC00607F

Search articles by author

Spotlight

Advertisements