Trichostachine

A new natural imino-alcohol, 3,4-dihydroxy-2,5-dihydroxymethylpyrrolidine (1) has been isolated from the roots and leaves of Derris elliptica. Its structure and configuration have been settled principally by n.m.r. and mass spectrometry. It appears to be the first example of the occurrence of an iminopolyol in the vegetable kingdom. Trichostachine (2) has been found in the fruit of Piper guineense Schum,... 

This section summarises recent work on alkaloids containing the pyrrolidine nucleus. A short review concerning the synthesis of this group has appeared. A variety of Labiatae plants have been screened and some of them have been shown to contain pyrrolidine alkaloids. Cuskhygrine has been found in the roots of three Datura species and stachydrine has been obtained from Capparis spinosa3 The structure of trichostachine (1) Piper trichostachyon) has been elucidated by spectral means and confirmed by synthesis. Ficine (5), an interesting flavonoid alkaloid, has been synthesised. Friedel-Crafts reaction between... 

Sigmatropic rearrangements of ynamines followed by dehydrosulfenylation have been applied to the synthesis [61] of piperine (25) and trichostachine (24) (Scheme 17). 

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