Ramachandra Row, L. ; Subba Rao, G. S. R. ; Sundara Ramaiah, T. (1964) Chemistry of terminalia species-IX: The structure of methyl anhydro tomentosate Tetrahedron, 20 (4). pp. 999-1004. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)98435-2
Abstract
Methyl triacetyltomentosate by loss of water (1 mole) with POCl3-pyridine yields methyl anhydrotomentosate which is not identical with methyl dehydroarjunolate. The anhydro compound yields a molecule of formaldehyde in OsO4-Pb(OAc)4 oxidation, establishing an exocyclic double bond, probably situated at C-20 through a methyl shift. It suffers facile catalytic reduction to give methyl dihydroanhydrotomentosate which resembles methyl asiatate in m.p., m.m.p., and lactonization but a comparison of their IR spectra reveals that probably inversion at C-19 has taken place during the Wagner-Meerwein methyl rearrangement.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 55726 |
| Deposited On: | 19 Aug 2011 03:16 |
| Last Modified: | 17 Jul 2012 07:26 |
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