Homalium alkaloids isolation

The Homalium Alkaloids Isolation, Synthesis, and Absolute Configuration Assignment... 

Homalium alkaloids isolation, synthesis and absolute configuration assignment, 74, 121 (2015)... 

Stephen Davies andjames Thomson from the Department of Chemistry at the University of Oxford describe in Chapter 2 the isolation, structural elucidation, and synthesis of homalium alkaloids. This relatively small class of alkaloids currently comprises only four members. Although homalium alkaloids have been known for more than 45 years, so far they were not covered in our series. 

Investigation of Allophylus cobbe, Homalium foetidium, and Aglaia species for alkaloid content has so far yielded only simple aromatic amide derivatives. An interesting phenethylamine-sesquiterpenoid alkaloid, elegantine, has been isolated from Saussurea salsa and S. elegansV NJV-Dimethylamino-p-hydroxy-phenethylamine is the first alkaloid to be extracted from marine algae. ... 

Details concerning the structural elucidation of homaline (57) and the related alkaloids hopromine, hoprominol, and hopromalinol, isolated from Homalium pornyense, have been published. The related spermidine alkaloid periphyllene (58) has been recently isolated from the leaves of Peripterygia marginata. Its structure and absolute stereochemistry were determined by spectral and chemical-degradation studies. 

The history of the isolation and structure elucidation of the spermine alkaloids dates from 1968, when homaline was isolated from the leaf of Homalium pronyense (Flacourtiaceae). The total synthesis of this alkaloid was reported in 1982, and the chemical structure, including absolute stereochemistry, was confirmed [2]. 

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