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Volumn 2, Issue 11, 2000, Pages 1513-1516

Studies in Marine Polypropionate Synthesis: Total Synthesis of (-)-Baconipyrone C

Author keywords

[No Author keywords available]

Indexed keywords

BACONIPYRONE C; BIOLOGICAL FACTOR; POLYMER; PROPIONIC ACID DERIVATIVE; PYRONE DERIVATIVE;

EID: 0034203562     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000027n     Document Type: Article
Times cited : (47)

References (36)
  • 1
    • 0030131103 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75. (b) Davies-Coleman, M. T.; Garson, M. J. Nat. Prod. Rep. 1998, 15, 477.
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 75
    • Faulkner, D.J.1
  • 8
    • 0442299641 scopus 로고    scopus 로고
    • note
    • (b) A reexamination of S. baconi, as reported by Garson (ref 1b), failed to detect any baconipyrones, such that they may conceivably be artifacts of the isolation process rather than biosynthetically related metabolites to the siphonarins. This may also hold for other polypropionates obtained from siphonariids, as with muamvatin (ref 6b) and the denticulatins (ref 6c).
  • 20
    • 0442330812 scopus 로고    scopus 로고
    • note
    • The double Swern oxidation was routinely performed by employing oxalyl chloride (5 equiv), DMSO (10 equiv), and triethylamine (15 equiv). After warming from -78 to -20°C. the reaction mixture was quenched with a mixture of anhydrous hexane/toluene (3:1), followed by filtration through Celite, to obtain spectroscopically pure diketone. Other procedures (Dess-Martin, TPAP) led to undesired cyclisations of mono-oxidized products.
  • 24
    • 0442283766 scopus 로고    scopus 로고
    • note
    • This also avoided the presence of sulfur residues in the subsequent hydrogenolysis of the benzyl group, which proved to be problematic due to catalyst poisoning.
  • 35
    • 85088000647 scopus 로고    scopus 로고
    • note
    • D values for baconipyrone C are now also quite similar to that recorded for the normethyl compound, baconipyrone D (4).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.