Abstract
The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 having an acryloxy moiety at the termini, carbon monoxide, and TTMSS (or tin hydride) was achieved under free radical reaction conditions. The allyltin mediated reaction of 1 also proceeded successfully to furnish 2-allyl-substituted 4-oxolactones 3 in moderate to good yields. In this n + 1 type macrocyclization, high dilution conditions ([1] = 0.005-0.01 M) are beneficial for both the intermolecular trapping of CO and the intramolecular acyl radical addition to the C-C double bond.
Original language | English |
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Pages (from-to) | 14615-14626 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 53 |
Issue number | 43 |
DOIs | |
State | Published - 27 Oct 1997 |