Abstract
The iodocarbocyclization of 4-pentenylmalonate 1 having a substituent at the 2 or 3 position effectively proceeded by treating 1 with I2 and Ti(OtBu)4 in the presence of CuO. Stereoelectronic effect of the subtituent at allylic position on diastereoselectivity was notable. As an application of the present reaction, the efficient synthesis of cyclosarkomycin 7 was achieved.
| Original language | English |
|---|---|
| Pages (from-to) | 1059-1062 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 35 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 1994 Feb 14 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Kitagawa, O., Inoue, T., & Taguchi, T. (1994). Diastereoselective iodocarbocyclization of 4-pentenylmalonate derivatives: Application to cyclosarkomycin synthesis. Tetrahedron Letters, 35(7), 1059-1062. https://doi.org/10.1016/S0040-4039(00)79965-5