Two Syntheses of FF-MAS

Abstract

[reaction: see text] Follicular fluid-meiosis activating sterol (FF-MAS) has been shown to be an efficient inducer of meiotic maturation. It can potentially be used for improvements of in vitro fertilization techniques. Two short synthesis of FF-MAS are presented in this article. Both syntheses are based on microbiological degradations of sterol side chains. FF-MAS can be synthesized in nine steps from commercially available starting materials by both routes.

Metabolism and Biological Activities of 4-Methyl-Sterols

“…Sterol biosynthetic flux analyzed in mice revealed a high rate of FF-MAS and T-MAS synthesis that defines cell-type specific pathways and also raised new hypothesis about the fate of T-MAS in testes (forming zymosterol, another sterol, a steroid hormone, or an excreted product) [45]. Synthetic FF-MAS and T-MAS were developed for further biological studies [46,47]. Human genetic diseases known as sterolosis are characterized by a dramatic accumulation of sterol intermediates including the immediate cholesterol precursors lathosterol and desmosterol (their accumulation causing lathosterolosis and desmosterolosis, respectively) but also of C4-SBIs causing severe alterations in development at early (embryo malformation) or later stages (skin anatomical changes) [48,49,50].…”

Efficient Synthesis of Thiazole-Fused Bisnoralcohol Derivatives as Potential Therapeutic Agents

“…This product is formed in a quantitative yield. The reaction of the epoxyketone (6) with different thiourea derivatives formed fused thiazole compounds (Scheme 1). We used acetic acid as a promoter and solvent for this reaction.…”

“…Furthermore, single-crystal X-ray diffraction of three compounds, 8 (CCDC: 2304175), 23 (CCDC: 2304173), and 32 Scheme 1. Synthesis of Fused Thiazolo-Bisnoralcohol Derivatives (7−33) by Reacting Substituted Thioureas with Epoxy-Bisnoralcohol (6), Which Was Synthesized from Commercially Available Bisnoralcohol (5) Figure 2. Design of potential antineoplastic compounds based on our previous results.…”

“…Synthesis of Thiazolo-Bisnoralcohol. Synthesis of Epoxy-Bisnoralcohol (6). Bisnoralcohol (1 mmol), dichloromethane (3 mL), methanol (4 mL), 10% NaOH (0.28 mL), and 30% H 2 O 2 (0.56 mL) were combined and stirred for 12 h in a round-bottom flask.…”

A Concise Account of Various Approaches for Stereoselective Construction of the C-20(H) Stereogenic Center in Steroid Side Chain

“…Sterols with additional methyl groups on the ring skeleton are found in many plants and fungi and abundantly in the wool fat of sheep. The best examples are lanosterol 6, agnosterol 7, and 4,4′-dimethyl-5α-cholesta-8,14,24-trien-3β-ol 8 [FF-MAS (follicular fluid meiosis-activating sterol)], a naturally occurring sterol isolated 6 from human follicular fluid (Figure 3).…”