DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES - APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS

Authors
KITAGAWA O INOUE T TAGUCHI T
Citation
O. Kitagawa et al., DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES - APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS, Tetrahedron letters, 35(7), 1994, pp. 1059-1062
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
7
Year of publication
1994
Pages
1059 - 1062
Database
ISI
SICI code
0040-4039(1994)35:7<1059:DIO4D>2.0.ZU;2-D
Abstract
The iodocarbocyclization of 4-pentenylmalonate I having a substituent at the 2 or 3 position effectively proceeded by treating I with I-2 an d Ti(OtBu)(4) in the presence of CuO. Stereoelectronic effect of the s ubtituent at allylic position on diastereoselectivity was notable. As an application of the present reaction, the efficient synthesis of cyc losarkomycin 7 was achieved.