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Titolo:
New highly stereoselective synthesis of (E)-droloxifene via selective protection of 3,4 '-dihydroxybenzophenone and McMurry reaction
Autore:
Gauthier, S; Sanceau, JY; Mailhot, J; Caron, B; Cloutier, J;
Indirizzi:
Ctr Hosp Univ Quebec, CHUL, Res Ctr, Lab Mol Endocrinol,Med Chem Div, Quebec City, PQ G1V 4G2, Canada Ctr Hosp Univ Quebec Quebec City PQ Canada G1V4G2 ty, PQ G1V 4G2, Canada Univ Laval, Quebec City, PQ G1V 4G2, Canada Univ Laval Quebec City PQ Canada G1V 4G2 Quebec City, PQ G1V 4G2, Canada
Titolo Testata:
TETRAHEDRON
fascicolo: 5, volume: 56, anno: 2000,
pagine: 703 - 709
SICI:
0040-4020(20000128)56:5<703:NHSSO(>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
LOW-VALENT TITANIUM; METASTATIC BREAST-CANCER; BONE LOSS; OVARIECTOMIZED RATS; DROLOXIFENE; TAMOXIFEN; ESTROGEN;
Keywords:
stereoselection; McMurry reactions; anticancer agents; regioselection;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
49
Recensione:
Indirizzi per estratti:
Indirizzo: Gauthier, S Ctr Hosp Univ Quebec, CHUL, Res Ctr, Lab Mol Endocrinol,Med Chem Div, Quebec City, PQ G1V 4G2, Canada Ctr Hosp Univ Quebec Quebec City PQ Canada G1V 4G2 G2, Canada
Citazione:
S. Gauthier et al., "New highly stereoselective synthesis of (E)-droloxifene via selective protection of 3,4 '-dihydroxybenzophenone and McMurry reaction", TETRAHEDRON, 56(5), 2000, pp. 703-709

Abstract

A new, highly stereoselective synthesis of (E)-droloxifene is reported. Deprotection of 3,4'-dimethoxybenzophenone and selective pivaloylation of the3'-phenolic position gave 4-hydroxy-3'-(trimethylacetoxy)benzophenone. A McMurry reaction between the preceding benzophenone and propiophenone gave the (E)-olefin as a major product (14:1 E/Z ratio in crude reaction), which was then alkylated with 2-dimethylaminoethyl chloride and deprotected to yield (E)-droloxifene with a >100:1 E/Z ratio (5 steps, 13%). Attempts to usethis strategy as a suitable stereoselective method to obtain (Z)-droloxifene were not successful. (C) 2000 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/03/20 alle ore 00:11:20