Synthesis of estradiol backbone mimics via the Stille reaction using copper(II) oxide as co-reagent

Tetrahedron Letters

Volumn 52, Issue 2, 2011, Pages 209-211

  Flöistrup, Erik ^a   Goede, Patrick ^b   Strömberg, Roger ^a   Malm, Johan ^c  

^a KAROLINSKA INSTITUTE   (Sweden)

^b SWEDISH DEFENCE RESEARCH AGENCY   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2 TRIMETHYLSTANNYL 6 METHOXYBENZO[B]THIOPHENE; BENZOTHIOPHENE DERIVATIVE; CUPRIC OXIDE; ESTRADIOL; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CATALYSIS; CROSS COUPLING REACTION; DRUG SYNTHESIS; STILLE REACTION;

EID: 78650006372     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.144     Document Type: Article

References (22)

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22. Method B: A stirred mixture of bromo component (2.0 mmol), tris(dibenzylidene-acetone)dipalladium (0.1 mmol) and trifurylphosphine (0.4 mmol, 5 mol %) in DMF (8 mL) was purged with argon for 10 min. 4-trimethyl-stannylbenzaldehyde (0.67 g, 2.5 mmol) was added to the reaction mixture and heating was set to 65 °C. When no further development could be observed (TLC), ethyl acetate and activated carbon were added and the mixture was set to reflux for 15 min, after which it was filtered through a short pad of Celite (1 cm) on silica (1 cm) in a glass filter funnel. The filtrate was evaporated and the residue was further purified on HPLC. Yields were determined using HPLC as described above under Method A.