Abstract
(Chemical Equation Presented) A highly stereocontrolled, convergent synthesis of the A/B-ring fragment of gambieric acids (GAs) has been developed on the basis of (i) a Suzuki-Miyaura coupling of the C1-C6 alkylborate and the C7-C17 vinyl iodide and (ii) a diastereoselective haloetherification for the construction of the A-ring tetrahydrofuran as key steps. Inspection of the 1H and 13C NMR chemical shifts of the synthesized A/B-ring model compounds led to a stereochemical reassignment of the absolute configuration of the polycyclic ether core of GAs. This structure revision was further supported by a synthesis of the A/BC-ring model compound of gambieric acid B and a comparison of its 1H and 13C NMR data with those of the natural product.
Original language | English |
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Pages (from-to) | 4024-4040 |
Number of pages | 17 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2009 Jun 5 |
ASJC Scopus subject areas
- Organic Chemistry