Total synthesis of aspercyclides A and B via intramolecular oxidative diaryl ether formation.

Total synthesis of aspercyclides A and B via intramolecular oxidative diaryl ether formation.

Organic letters (2012-08-09)

Tatsuya Yoshino, Itaru Sato, Masahiro Hirama

ABSTRACT

A highly efficient total synthesis of the 11-membered cyclic aspercyclides A (1) and B (2) has been achieved by chemo- and regioselective intramolecular oxidative C-O bond formation from differently substituted diphenols.

MATERIALS

Product Number

Brand

Product Description

31685

Sigma-Aldrich

Diethyl ether, puriss., dried over molecular sieve (H₂O ≤0.005%), ≥99.8% (GC)

296082

Sigma-Aldrich

Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%

91238

Supelco

Diethyl ether, analytical standard

179272

Sigma-Aldrich

Diethyl ether

346136

Sigma-Aldrich

Diethyl ether, ACS reagent, anhydrous, ≥99.0%, contains BHT as inhibitor

676845

Sigma-Aldrich

Diethyl ether, ACS reagent, ≥98.0%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor

673811

Sigma-Aldrich

Diethyl ether, anhydrous, ACS reagent, ≥99.0%, contains BHT as inhibitor

32203

Sigma-Aldrich

Diethyl ether, contains BHT as inhibitor, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

346144

Sigma-Aldrich

Diethyl ether, reagent grade, ≥98%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor

24004

Sigma-Aldrich

Diethyl ether, puriss., contains ~5 mg/L 2,6-di-tert.-butyl-4-methylphenol as stabilizer, meets analytical specification of Ph. Eur., BP, ≥99.5% (GC)

309966

Sigma-Aldrich

Diethyl ether, suitable for HPLC, ≥99.9%, inhibitor-free