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Volumn , Issue 8, 2007, Pages 1294-1298

Refined protocols for the preparation of 3-alkoxy-2,5-dihydrofurans, allylic oxidation to β-alkoxybutenolides and short synthesis of (±)-annularin H

(2) Brasholz, Malte a Reissig, Hans Ulrich a

a FREIE UNIVERSITÄT BERLIN (Germany)

Author keywords

Allenes; Allylic oxidation; Butenolides; Dihydrofurans; Gold catalysis

Indexed keywords

3 ALKOXY 2,5 DIHYDROFURAN DERIVATIVE; ANNULARIN H; BETA ALKOXYBUTENOLIDE DERIVATIVE; BUTENOLIDE; FURAN DERIVATIVE; GOLD CHLORIDE; MANGANESE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 34249823085 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-977456 Document Type: Article

Times cited : (44)

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35
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- Typical Procedure for the Au(I)-Catalyzed Cyclization: Preparation of Compound 4g Methoxyallene (0.35 mL, 294 mg, 4.19 mmol) was dissolved in Et2O, 5 mL) at -40 °C. n-BuLi (1.40 mL, 2.5 M in hexane, 3.50 mmol) was added, the mixture was stirred for 20 min and then cooled to -78 °C. A solution of ketone 1g (180 mg, 1.15 mmol) in Et2O (2 mL) was slowly added and the mixture was stirred at -78 °C for 2.5 h. Then H2O (10 mL) was added and the mixture was warmed to r.t. The layers were separated and the aqueous layer was extracted with Et2O (3x, The combined organic layers were dried (MgSO4, filtered, and evaporated. Drying at 0.1 mbar provided the allenyl alcohol as a yellow oil (285 mg, quant, The crude product (max. 1.15 mmol) was dissolved in CH 2Cl2 (17mL, Pyridine (15 μL, 15 mg, 190 μmol) and AuCl (13 mg, 56 umol) were added with rapid stirring. After 1 h. TLC show
- 4 (226.3): C, 63.70; H, 8.02. Found: C, 63.47; H, 8.11.

36
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- Typical Procedure for the Allylic Oxidation: Preparation of(±)-AnnularinH(17) Dihydrofuran 16 (520 mg, 2.03 mmol) was dissolved in MeCN (22 mL, Then, Cs2CO3 (335 mg, 1.03 mmol) and powdered 4 Å MS (1.02 g) were added. After cooling to 0 °C, TBHP (1.90 mL, 5.5 M solution in nonane, 10.5 mmol) and Mn(OAc) 3-2H2O (27 mg, 101 μmol) were added and the flask was equipped with a balloon of O2. The mixture was vigorously stirred at 0 °C for 72 h, then poured into an aqueous solution of FeS0 4-7H2O (ca. 2.5 g in 30 mL H2O, rinsing with EtOAc (10 mL, After 10 min of stirring, the mixture was filtered through Celite® with the aid of EtOAc (50 mL, The filtrate layers were separated and the aqueous layer was extracted with EtOAc (5x, The combined organic layers were dried MgSO4, filtered, and evaporated to dryness. The residue was dissolved in acetone-H
- 4 (184.2): C, 58.69; H, 6.57. Found: C, 58.25; H, 6.56. The analytical data are in agreement with those given in ref. 15.

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