Traceless solid-phase synthesis of heterosteroid framework

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2647-2649

  Hong, Bor Cherng ^a   Chen, Zhong Yi ^a   Chen, Wei Hung ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BENZO(D)CYCLOPENTA(E) 3H AZIN 8 OL; BENZO(D)CYCLOPENTA(E)-3H-AZIN-8-OL; BENZOPYRAN DERIVATIVE; CYCLOPENTA(C) 4H CHROMEN 8 OL; CYCLOPENTA(C)-4H-CHROMEN-8-OL; CYCLOPENTANE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FULVENE; QUINOLINE DERIVATIVE; STEROID;

ARTICLE; CELL CULTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; DRUG SCREENING; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BENZOPYRANS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOPENTANES; DRUG SCREENING ASSAYS, ANTITUMOR; INDICATORS AND REAGENTS; QUINOLINES; STEROIDS; TUMOR CELLS, CULTURED;

EID: 0034710490     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006180z     Document Type: Article

References (33)

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22. Purchased from Aldrich Chemical Co. (1.5 mmol/g) or Advanced ChemTech, Inc. (1.1 mmol/g, 100-200 mesh).
23. The reactions were conducted in Bio-Rad Econo-Pac Disposable columns. Agitation was accomplished by rotating the column with a rotary motor unless otherwise indicated. The extent of the coupling reaction was monitored by IR.
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25. The reaction was agitated in an ultrasonic bath.
26. In solution phase, this reaction was completed in a few minutes.
27. The purity of the products was determined by GC-MS and HPLC analysis.
28. 13C NMR spectrum.
29. The loading of the fulvene resin 3 was estimated to be ca. 0.4 mmol/g on the basis of the consumption amount of benzoquinones in the following hetero [6 + 3] reaction (assume 100% conversion in the reaction). On the basis of this loading number, we noticed that when slightly less than 1 equiv of benzoquinone was used in the last step, products 4 were isolated free of impurity as shown by HPLC. The following are selected overall yields of isolated products after four steps: 4Be (40%), 4Bj (42%), 4Bi (38%), 4B′k (32%). These yields are based on the initial loading of the amino polystyrene resin (1.1 mmol/g).
30. +) 264.0786, found 264.0781.
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