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Volumn , Issue 15, 2001, Pages 2851-2860

A short intramolecular Diels-Alder route to himbacine derivatives

Author keywords

Cycloadditions; Neurotransmitters; Receptors; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; HIMBACINE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034888263     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200108)2001:15<2851::AID-EJOC2851>3.0.CO;2-U     Document Type: Article
Times cited : (29)

References (51)
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    • The approach described in reference [9] also takes advantage of an all-encompassing IMDA
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    • note
    • We thank DSM Fine Chemicals (Geleen) for a generous gift of the enantiomerically pure material (98% ee according to Mosher's ester).
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    • note
    • The enantiomeric purity of (-)-13 was confirmed via chiral HPLC analysis (2,6-TBS-3-methyl-γ-cyclodextrin 50%/50% OV-1710).
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    • Substance 11 is rather unstable; while it can be usually stored on copper in the dark at 0 °C for a couple of weeks, some batches were found to decompose upon distillation. A more tedious but reliable procedure involves the use of Schwartz reagent (74% yield): E. Nigishi, T. Takahashi, Synthesis 1988, 1-19.
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    • The use of dimethyl-1-diazo-2-oxopropylphosphonate (ref. [25a]), prepared according to reference [25b], led to a high yield of a 4:1 mixture in favour of the cis derivative. -[25a] S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett. 1996, 521-522. -
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    • note
    • 1H NMR analysis using (S)-mandelic acid methyl ether as shift reagent.
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    • A similar Stille coupling (46% yield) involving (+)-2 has been described before in the context of the preparation of (+)-hamabiwalactone B (ref. [17]).
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    • note
    • For the sake of consistency the numbering of the acyclic precursor 5 is maintained in the cycloadducts 17 and in the subsequent intermediates.
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    • note
    • The α-orientation of the methoxy group has been assigned in the c-series, see footnote 39 in reference [8b]; see also reference [6c].
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    • note
    • Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-153103. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int.code+44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.