Pd(0)-mediated cross coupling of 2-iodoestradiol with organozinc bromides: A general route to the synthesis of 2-alkynyl, 2-alkenyl and 2-alkylestradiol analogs

Synlett

Volumn , Issue 7, 1999, Pages 1097-1099

  Mohanakrishnan, Arasambattu K ^a   Cushman, Mark ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Antitumor compounds; Cross coupling; Estradiol; Organozinc bromides; Palladium

Indexed keywords

ANTINEOPLASTIC AGENT; COLCHICINE; ESTRADIOL DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX; TUBULIN; ZINC BROMIDE;

ARTICLE; CATALYST; CROSS LINKING; DRUG BINDING SITE; DRUG CYTOTOXICITY; DRUG SYNTHESIS; MICROTUBULE ASSEMBLY;

EID: 0032811478     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2773     Document Type: Article

References (21)

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18. 2 in dry THF.
19. The corresponding Grignard reagent was not commercially available. It was prepared from propargyloxy trimethylsilane and ethylmagnesium bromide in THF.
20. The crude product was contaminated with 3,17-O-bis(tertbutyldimethylsilyl)estradiol. However, when the coupling reaction was carried out with the iodo compound 2 instead of 3, the corresponding 2-vinyl-3,17-bis(methoxymethyl)-estradiol was isolated in 89% yield as a pure compound.
21. 2: C, 73.22; H, 9.98. Found: C, 73.14; H, 10.26.