OXIDATION OF 3-BETA,28-DIACETOXY-18-LUPEN-21-ONE WITH PEROXY ACIDS - A WAY TO DES-E-LUPANE DERIVATIVES

Authors
KLINOTOVA E REJZEK M ZUNOVA H SEJBAL J KLINOT J URBAN J
Citation
E. Klinotova et al., OXIDATION OF 3-BETA,28-DIACETOXY-18-LUPEN-21-ONE WITH PEROXY ACIDS - A WAY TO DES-E-LUPANE DERIVATIVES, Collection of Czechoslovak Chemical Communications, 58(10), 1993, pp. 2505-2516
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
58
Issue
10
Year of publication
1993
Pages
2505 - 2516
Database
ISI
SICI code
0010-0765(1993)58:10<2505:OO3WPA>2.0.ZU;2-T
Abstract
Oxidation of 3beta,28-diaectoxy-18-lupen-21-one (I) and its 18beta,19b eta-epoxy derivative III with peracetic acid, catalyzed with strong ac ids, proceeds with cleavage of the bond between C-19 and C-21 under fo rmation of E-seco derivatives with hydroxyl and isobutyryl groups on C -18 (spiro lactones V - VII and acid VIII). Oxidative removal of the i sobutyryl fragment in spiro lactone VI by treatment with lead tetraace tate leads to the tetranor derivative - keto lactone XI which in an al kaline medium loses formaldehyde from C-17 to give des-E acid XVI.