A One-Pot Efficient Process for 16-Dehydropregnenolone Acetate

Abstract

A one-pot eco-friendly and efficient transformation of steroidal sapogenin diosgenin (1) and solasodine (2) to a commercially very important drug intermediate 16-dehydropregnenolone acetate (16-DPA, 9) was developed with an overall yield of 75%. This process can easily be exploited for industrial production.

A Simple Efficient Process for the Synthesis of 16-Dehydropregnenolone Acetate(16-Dpa)–A Key Steroid Drug Intermediate from Diosgenin

“…IR spectrum exhibited a band at 1715 cm -1 for this newly generated carbonyl functionality. 13 C NMR & microanalyses were in conformity with its molecular structure and formula C 31 H 46 O 7. Although some literature reveal the application of other oxidant like hydrogen peroxide in presence of catalyst/phase transfer catalysts etc [14]. CrO 3 is still regarded as an oxidant of choice, because of its high efficacy and low cost.…”

“…are synthesized from 16-dehydropregnenolone acetate (16-DPA) 1, barring a few which are obtained by total synthesis. The plant origin compounds solasodine 2 and its oxygen analogue diosgenin 3 ( Figure 1) are the two main ingredients from which 16-DPA is generally synthesized [4][5][6][7][8][9][10][11][12][13][14][15]. Due to the favorable climatic condition of North East region of India, diosgenin yielding dioscorea species of plants, viz., D. compositae and D. floribunda grow abundantly in the region which led us to investigate commercial exploitation of these plants through large scale production of 16-DPA starting from diosgenin.…”

“…Synthesis of 16-dehydropregnenolone acetate (16-DPA) 1 from solasodine 2 and diosgenin 3 has been reported by several workers in various literatures [4][5][6][7][8][9][10][11][12][13][14][15]. For the conversion of this spirostanic compound, diosgenin (22-iso-5-spirostane-3β-ol) into 16-DPA (3β-acetoxy-pregn-5,16-diene-20-one) 1, it must be isomerized first to furostenol derivative pseudodiosgenin diacetate (3β,26-diacetoxyfurosta-5,20(22)-diene) 4, through acetolysis (Figure 2), which on subsequent oxidation of the 20(22) enolic double bond followed by hydrolytic degradation furnishes 16-DPA [4][5][6][7][8][9][10][11][12][13][14][15].…”

“…For the conversion of this spirostanic compound, diosgenin (22-iso-5-spirostane-3β-ol) into 16-DPA (3β-acetoxy-pregn-5,16-diene-20-one) 1, it must be isomerized first to furostenol derivative pseudodiosgenin diacetate (3β,26-diacetoxyfurosta-5,20(22)-diene) 4, through acetolysis (Figure 2), which on subsequent oxidation of the 20(22) enolic double bond followed by hydrolytic degradation furnishes 16-DPA [4][5][6][7][8][9][10][11][12][13][14][15]. Chemical transformations of spirostanic compounds also find importance towards the synthesis of plant growth promoting substances including ecdysteroids and some furostenols having significant phytotoxicity [18].…”

Alterações reprodutivas em ratos machos expostos perinatalmente aos frutos da Solanum lycocarpum

“…It can give origin to the compound 3-B-acetoxypregna-5-16-dienone, key starting source for progesterone production 1 and the compound 16-dehydroepiandrosterone, key starting source for androgen production 2 . Previous studies demonstrated that solasodine promotes antispermatogenic activity when administered to dogs (20 mg/kg for 30 days) 3 and to monkeys (150 mg/kg for 150 days) 4 .…”