Acacia sutherlandii

Then the synthetic 32 was converted to the cyanoglucoside sutherlandin (44) which was isolated from leaves of Acacia sutherlandii. Acetylation of a diastereomeric mixture of 32 gave the corresponding acetate which was subjected to the hydrogenation and the subsequent oxidation to yield the a-acetoxyl ketone (45, 84% overall yield from the acetate of 32). The Homer-Emmons reaction of 45 using diethyl cyanomethylphosphonate furnished (Z)-46a (33% yield from 45) and ( )-46b (31% yield from 45). Deprotection of the presumably desired (Z)-46a afforded (Z)-44 (76% yield), whose C-NMR spectra were identical with those of the natural sutherlandin (44) (Fig. 6). 

Swenson Acacia sutherlandii Leguminosae Australia sutherlandin (IS) ... 

Recently, sutherlandin (15), an unusual non-cyanogenic cyanoglucoside which has an isopentane skeleton was isolated from Acacia sutherlandii (Leguminosae) [22]. Following this, similar glucosides were reported [23-28] (Table 1 and Figure 1). Interestingly, all compounds have the same carbon skeleton. 

Sutherlandin (57), a compound related by structure to the series of compounds derived from leucine, and in particular to certain cyanolipids, is weakly cyanogenic. This compound co-occurs in Acacia sutherlandii with proacacipetalin and the dimer of the two compounds (Swenson, 1986 Swenson... 

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