First synthesis of segetalins B and G: two cyclopentapeptides with estrogen-like activity

New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines

“…In a continuation of our work regarding the structure-activity relationships of the segetalins, 27,28 there remains a need to reduce the number of steps to obtain the N-boc piperazine (1 0 R)-2. Thus, by taking note of the work of Watson et al 29 and of Vetuschi et al 30 we have developed a third strategy of synthesis starting from O-benzyl-D-serine (Scheme 8).…”

“…The desired compound (S)-10 (10.1 g, 78%), yellow oil, was achieved after silica gel column chromatography (eluent: cyclohexane/ethyl acetate, 7:3). ½a 28 …”

Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review

“…Total synthesis has subsequently given segetalins A (Sonnet et al 2001), B and G (Sonnet et al 2003), C (Dahiya and Kaur 2008), D (Dahiya 2007) and E (Dahiya and Kaur 2007).…”

Application of high-speed counter-current chromatography for preparative separation of cyclic peptides from Vaccaria segetalis

“…Cyclic peptides obtained from the seeds of V. segetalis have become a subject of interest because of bioactivities including oestrogen-like activity [6,7], vasorelaxant activity [8]. Although these cyclic peptides can be chemically synthesized [9,10], a large amount of organic solvents were used and also toxic waste in organic synthesis was produced. Therefore, development of an efficient method for the preparation of these compounds from the natural sources is warranted.…”