The total synthesis of calcium atorvastatin.

A practical and convergent asymmetric route to calcium atorvastatin (1) is reported. The synthesis of calcium atorvastatin (1) was performed using the remote 1,5-anti asymmetric induction in the boron-mediated aldol reaction of β-alkoxy methylketone (4) with pyrrolic aldehyde (3) as a key step. Calcium atorvastatin was obtained from aldehyde (3) after 6 steps, with a 41% overall yield.

1-Benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate.

The pyrrolidine-2,5-dione ring in the title compound, C(15)H(15)NO(6), is in a twisted conformation with the acetyl C atoms projecting to opposite sides of the ring. The acetyl groups lie to opposite sides of the five-membered ring. The benzene ring is roughly perpendicular to the heterocyclic ring, forming a dihedral angle of 76.

5-(4-Fluoro-phen-yl)-2,2,6-trimethyl-4H-1,3-dioxin-4-one.

The 1,3-dioxine ring in the title compound, C(13)H(13)FO(3), is in a half-boat conformation with the methyl-bonded C atom 0.612 (2) Å out of the plane defined by the remaining five atoms.

2,2,6-Trimethyl-5-[2-(4-methyl-phen-yl)ethyn-yl]-4H-1,3-dioxin-4-one.

The 1,3-dioxin-4-one ring in the title compound, C(16)H(16)O(3), is in a half-boat conformation with the quaternary O-C(CH(3))(2)-O atom lying 0.546 (1) Å out of the plane defined by the remaining five atoms. The crystal structure is consolidated by C-H⋯O contacts that lead to supra-molecular layers.

Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.

A convenient, mild and highly stereoselective method for C-glycosidation (alkynylation) of D-glucal with various potassium alkynyltrifluoroborates, mediated by BF3x OEt2 and involving oxonium intermediates, preferentially provides the alpha-acetylene glycoside products with good yields.

Stereoselective synthesis of enynes by nickel-catalyzed cross-coupling of divinylic chalcogenides with alkynes.

(Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.