A new method for hydroxymethylene peptide isostere synthesis: Asymmetric synthesis of statine

The syntheses of [13C6] and [phenyl‐14C(U)]BMS‐816336, an inhibitor of 11β‐hydroxysteroid dehydrogenase type 1, for type 2 diabetes

“…3.10 | Methyl 2-(-6-[ 13 C 6 ]phenylspiro[adamantane-2,2'- [1,3] dioxolan]-6-yl)acetate, 12 12,13 To 6-[ 13 C 6 ]phenylspiro[adamantane-2,2′- [1,3]dioxolan]-6-yl acetate, 11, (1.05 g, 3.1 mmol) in a dry 100 mL flask with stir bar under nitrogen was added zinc triflate (60 mg, 0.17 mmol), DCM (10.3 mL), and 1-(tert-butyldimethylsilyloxy)-1methoxyethene (0.73 mL, 630 mg, 3.3 mmol). The reaction was stirred at room temperature overnight.…”

Synthesis of γ‐Aminobutyric Acid Analogs

“…The phenyl glycine-derived alkylated oxazinone (417) was alkylated to yield (418) and reduced to the lactol acetate (419), which undergoes coupling with the ketene silyl acetals or allyl silanes [305] in the presence of a Lewis acid to afford the corresponding product (420) (Scheme 14.115). In the case of the allyl silanes, the reaction proceeds with good to excellent stereoselectivity and yields.…”

Stereoselective synthesis of γ-amino acids

“…241 Williams et al 242 have reported the asymmetric synthesis of statine 23 and cyclohexylstatine 26 from commercially available glycine templates (2R,3S)-diphenyloxazinone 634. Thus, alkylation of lithium enolate derived from 634 afforded the alkylated products 635a and 635b in high diastereoselectivity, which by treatment with DIBAL-H followed by an acetylation reaction gave hemiacetals 636a and 636b.…”