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

Scheduled maintenance work on Wednesday 21st October 2020 from 07:00 AM to 07:00 PM (BST).

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 65, 2019
Previous Article Next Article

A counterintuitive stereochemical outcome from a chelation-controlled vinylmetal aldehyde addition leads to the configurational reassignment of phormidolide A

Author affiliations

Abstract

As part of our ongoing studies towards the total synthesis of phormidolide A (1), we explored the chelation-controlled vinylmetal addition of iodide 2 to aldehyde 3 to install the reported 17S configuration. While the stereochemical outcome of this reaction was opposite to that expected, detailed NMR comparisons with the previously reported triacetonide derivative of phormidolide A (18) highlighted that the major adduct was a better match to the natural product. The synthesis of three model acetonides and detailed spectroscopic comparisons to the triacetonide derivative of phormidolide A supports a reassignment of seven of the 11 stereocentres in phormidolide A (1a).

Graphical abstract: A counterintuitive stereochemical outcome from a chelation-controlled vinylmetal aldehyde addition leads to the configurational reassignment of phormidolide A

Back to tab navigation

Supplementary files

Article information


Submitted
02 Jul 2019
Accepted
23 Jul 2019
First published
23 Jul 2019

Chem. Commun., 2019,55, 9717-9720
Article type
Communication

A counterintuitive stereochemical outcome from a chelation-controlled vinylmetal aldehyde addition leads to the configurational reassignment of phormidolide A

N. Y. S. Lam, G. Muir, V. R. Challa, R. Britton and I. Paterson, Chem. Commun., 2019, 55, 9717
DOI: 10.1039/C9CC05067A

Social activity

Search articles by author

Spotlight

Advertisements