Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation

Kiyoto Nagahara, Ilhyong Ryu, Hiroshi Yamazaki, Nobuaki Kambe, Mitsuo Komatsu, Noboru Sonoda, Akio Baba

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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 languageEnglish
Pages (from-to)14615-14626
Number of pages12
JournalTetrahedron
Volume53
Issue number43
DOIs
StatePublished - 27 Oct 1997

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    Nagahara, K., Ryu, I., Yamazaki, H., Kambe, N., Komatsu, M., Sonoda, N., & Baba, A. (1997). Synthesis of macrocyclic ketoesters by an n + 1 strategy based on free-radical carbonylation. Tetrahedron, 53(43), 14615-14626. https://doi.org/10.1016/S0040-4020(97)01048-X