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 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Diastereoselective iodocarbocyclization of 4-pentenylmalonate derivatives : Application to cyclosarkomycin synthesis. / Kitagawa, Osamu; Inoue, Tadashi; Taguchi, Takeo.
In: Tetrahedron Letters, Vol. 35, No. 7, 14.02.1994, p. 1059-1062.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diastereoselective iodocarbocyclization of 4-pentenylmalonate derivatives
T2 - Application to cyclosarkomycin synthesis
AU - Kitagawa, Osamu
AU - Inoue, Tadashi
AU - Taguchi, Takeo
PY - 1994/2/14
Y1 - 1994/2/14
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0028349807&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0028349807&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)79965-5
DO - 10.1016/S0040-4039(00)79965-5
M3 - Article
VL - 35
SP - 1059
EP - 1062
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 7
ER -