Dasai, Manoj C. ; Singh, Chandan ; Chawla, H. P. S. ; Sukh Dev, (1982) Higher Isoprenoids-XII: Partial syntheses from cycloartenol, cyclolaudenol-Part 4: A novel method for functionalization of C-4 methyl in triterpenoids, and synthesis of cyclodeucalanone Tetrahedron, 38 (1). pp. 201-208. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/0...
Related URL: http://dx.doi.org/10.1016/0040-4020(82)85066-7
Abstract
A general method for selective oxygenation of C-4-Me in triterpenes, leading finally to 4 α -carboxyl/4 α -hydroxymethyl functionalities, is described. The key-step involved is phytolysis of hypoiodite derived from 3 β-hydroxymethyl derivative of the triterpene. The method is illustrated by the conversion of cyclolaudanone (1) into methyl 3-oxo-cyclolaudan-29-oate (2). The latter has been converted into the known cycloeucalanone (3) by a simple sequence of reactions.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 59192 |
| Deposited On: | 03 Sep 2011 11:47 |
| Last Modified: | 03 Sep 2011 11:47 |
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