Use of olefin templates in queued chemical transformations using late transition metal catalysis. Total synthesis of cis and trans bupleurynol via a single multireaction sequence

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2913-2916

  Ghasemi, Haleh ^a   Antunes, Luis M ^a   Organ, Michael G ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 BROMO 2 IODOETHYLENE; ALCOHOL DERIVATIVE; ALKENE; BUPLEURYNOL; ETHYLENE DERIVATIVE; PALLADIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; PROTECTION; SEQUENCE ANALYSIS; SYNTHESIS;

EID: 4444284414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0489853     Document Type: Article

References (23)

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12. For an example of the use of olefin templates to prepare olefin intermediates that were elaborated into ethanolamines via a "libraries from libraries" strategy, see: Organ, M. G.; Kaldor, S. W.; Dixon, C.; Parks, D. J.; Singh, U.; Lavorato, D. J.; Isbester, P. K.; Siegel, M. G. Tetrahedron Lett. 2000, 41, 8407-8411.
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14. (b) A similar approach was used by us recently to prepare (13E,15E,18Z,20Z)-1-hydroxypentacosa-13,15,18,20-tetraen-11-yn-4-one 1-acetate; see: Organ, M. G.; Ghasemi, H. J. Org. Chem. 2004, 69, 695-700.
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20. 22O 242.1671, found 242.1657. Spectra compared identically with that reported for the compound from its isolation (see ref 11).
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23. 22O 242.1671, found 242.1668. Spectra compared identically with that reported for the compound from its isolation (See ref 11).