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Volumn 6, Issue 11, 2004, Pages 1817-1820

Formal synthesis of (±)-guanacastepene A: A tandem ring-closing metathesis approach

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; GUANACASTEPENE A; OXYGEN; UNCLASSIFIED DRUG; DITERPENE;

EID: 2942629125     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049452x     Document Type: Article
Times cited : (84)

References (54)
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    • Ketone 5 was prepared by acidic hydrolysis of the corresponding silyl enol ether previously described . Piers, E.; Renaud, J.; Rettig, S. J. Synthesis 1998, 590.
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    • note
    • The stereochemical assignment at C14 was also based on extensive literature precedent (see for example refs 3a and 3c).
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    • 3 gave lower yields.
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    • note
    • The loss of isomer 15 with respect to 14 is probably due to the instability of the corresponding epoxide.
  • 48
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    • note
    • N2′ displacement by organocopper reagents is well documented, to our knowledge the ring-opening of vinyl oxiranes by alcohols in the presence of Lewis acid according to such a process is unprecedented.
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    • note
    • Attempts to achieve direct palladium- or rhodium-mediated allylic cleavage were unsuccessful. Details will be given in the full account of this work.
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    • note
    • The full description of the X-ray structure of 19 has been deposited with the Cambridge Crystallographic Data Centre, UK.
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  • 53
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    • note
    • The spectra of 18, 20, and 2 were compared with the copies of NMR spectra published as Supporting Information by Snider and co-workers (ref 3c).


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