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Volumn 3, Issue 4, 2008, Pages 495-504

A convenient synthesis of the central core of helioporins, seco-pseudopterosins and pseudopterosins via BCA-annulation sequence

Author keywords

Cuprate conjugate addition; Friedel crafts acylation; Helioporins; Pseudopterosins

Indexed keywords

HELIOPORINS A; HELIOPORINS E; PSEUDOPTEROSINS; SECO PSEUDOPTEROSINS; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 53149096252     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800300405     Document Type: Article
Times cited : (7)

References (72)
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    • note
    • The behaviour of compounds 10 and 15 towards the metallation reaction using nBuLi was very different. In the case of compound 15 the sequence o-metallation-capture with TMSCl allowed for the synthesis of 2,3-dimethoxy-4-(trimethylsilyl)-toluene (69-73% isolated yield depending on the reaction conditions). In the case of compound 10 only 17 was obtained under a variety of experimental conditions.
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    • Lower overall yields were obtained when the reaction was carried out in the absence of TMSCl. See: (a) Chuit C, Foulon JP, Norman JF. (1980) Action des dialkylcuprates de lithium sur les aldéhydes αβ- éthylénioues. Tetrahedron, 36, 2305-2310;
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