Beilstein J. Org. Chem.2008,4, No. 24, doi:10.3762/bjoc.4.24
self-assembly of nano-sized arjuna-bromolactone are reported.
Keywords: arjunolicacid; nanochemistry; renewable; self-assembly; triterpene; Introduction
Triterpenes are an important class of plant secondary metabolites derived from C30 precursors [1][2]. More than 100 triterpenoids with different
triterpenoids having a β-amyrin skeleton with certain amounts of α-amyrins is common in nature and has been explained by 1,2-CH3 migration during their biosynthesis [11]. The mixture of the triterpenic acids extractable from Terminalia arjuna contains arjunolicacid as the major component along with asiatic
-bromolactone 3 was isolated in pure form leaving 1.2 g of methyl asiatate (4) in the mother liquor (see Figure 1 for HPLC profiles).
Arjuna-bromolactone 3 (3.6 g) on stirring with Zn-dust (20 equivalents) in acetic acid at room temperature for 30 min produced arjunolicacid (3 g) in 97% isolated yield [12
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Graphical Abstract
Scheme 1:
(a) (i) Br2/AcOH, (ii) CH2N2, (iii) separation by crystallization, (b) Zn/AcOH/RT (c) LiBr/DMF. The...