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Volumn 6, Issue 2, 2011, Pages 459-473

Total synthesis and biological evaluation of a series of macrocyclic hybrids and analogues of the antimitotic natural products dictyostatin, discodermolide, and taxol

Author keywords

cytotoxicity; hybrids; natural products; total synthesis; tubulin

Indexed keywords

ANTI-CANCER AGENTS; ANTI-PROLIFERATIVE; BIOLOGICAL ASSAYS; BIOLOGICAL EVALUATION; CELL LINES; DICTYOSTATIN; DISCODERMOLIDE; DIVERSIFICATION STRATEGIES; ESTER LINKAGES; ETHER DERIVATIVES; FRANKENSTEINS; HUMAN CANCER CELLS; HYBRIDS; MACROCYCLICS; MACROLIDES; MARINE NATURAL PRODUCTS; METHOXY; MICROTUBULES; MODE OF ACTION; NATURAL PRODUCTS; POLYKETIDES; SIDE-CHAIN; STRUCTURAL COMPONENT; STRUCTURE ACTIVITY RELATIONSHIPS; SYNTHETIC ROUTES; TAXOTERE; TOTAL SYNTHESIS; TUBULIN;

EID: 79251515768     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000541     Document Type: Article
Times cited : (30)

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    • This rationalization was substantiated when an attempted reduction of the earlier β-hydroxy ketone with the enantiomeric (S)-CBS reagent failed to overturn the selectivity, and continued to generate the 1,3-anti-diol as the major diastereomer (4:1 d.r.).
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    • This isomerism of the dienoate had also been observed in the synthesis of 10,11-dihydro dictyostatin 22. A reversible 1,4-conjugate addition of DMAP being the most likely mechanism. Suitable conditions have since been developed to minimize this side-reaction, as reported in Ref. [34]. For the approach by Curran group's to solving this problem, see Ref. [24j].
    • This isomerism of the dienoate had also been observed in the synthesis of 10,11-dihydro dictyostatin 22. A reversible 1,4-conjugate addition of DMAP being the most likely mechanism. Suitable conditions have since been developed to minimize this side-reaction, as reported in Ref. [34]. For the approach by Curran group's to solving this problem, see Ref. [24j].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.