Synthesis of [2-C-13]-oleanolic acid and [2-C-13]-myricerone

Authors
Konoike, T Takahashi, K Kitaura, Y Kanda, Y
Citation
T. Konoike et al., Synthesis of [2-C-13]-oleanolic acid and [2-C-13]-myricerone, TETRAHEDRON, 55(52), 1999, pp. 14901-14914
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
52
Year of publication
1999
Pages
14901 - 14914
Database
ISI
SICI code
0040-4020(199912)55:52<14901:SO[AA[>2.0.ZU;2-G
Abstract
Synthetic way for C-13-labeled oleanolic acid I and myricerone 2 has been d eveloped, starting from the parent 1 and 2. The procedure involves ring ope ning and closure of the A rings of these oleanane triterpenes. C-13 was int roduced into the 2-position by C-13-MeLi as an isotope source. Chelation co ntrolled addition of methyllithium to alpha-hydoxypentanone 11 is a common crucial step for labeling of 1 and 2, and judicious choice of protecting gr oups is essential for 2. (C) 1999 Elsevier Science Ltd. All rights reserved .