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Volumn 49, Issue 9, 2008, Pages 1523-1526

Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D

Author keywords

Jerangolid D; Julia olefination; Kavain; Metathesis; Sulfoxide modified Julia olefination

Indexed keywords

DIMETHYL DEXTRO MALATE; ETHER DERIVATIVE; JERANGOLID D; KAWAIN; LACTONE DERIVATIVE; MALIC ACID DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 38649100324     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.113     Document Type: Article
Times cited : (25)

References (50)
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  • 29
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    • note
    • Alcohol 7 was obtained as a 12:1 mixture of the C6 and C5 monosilylated diols. See Table S-1 (Supplementary information).
  • 32
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    • note
    • For the reaction optimization, see Table S-2 (Supplementary information).
  • 34
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    • Use in total synthesis
    • Use in total synthesis. Holson E.B., and Roush W.R. Org. Lett. 4 (2002) 3719-3722
    • (2002) Org. Lett. , vol.4 , pp. 3719-3722
    • Holson, E.B.1    Roush, W.R.2
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    • Alternatively, initial reaction of GC-2 with the enol ether function rather than the acrylate might lead to a poorly active Fisher-type carbene. By shifting to an acetal, preferential addition on C1-C2 takes place
    • Stork G., Mook Jr. R., Biller S.A., and Rychnovsky S.D. J. Am. Chem. Soc. 105 (1983) 3741-3742 Alternatively, initial reaction of GC-2 with the enol ether function rather than the acrylate might lead to a poorly active Fisher-type carbene. By shifting to an acetal, preferential addition on C1-C2 takes place
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 3741-3742
    • Stork, G.1    Mook Jr., R.2    Biller, S.A.3    Rychnovsky, S.D.4
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    • note
    • Interestingly, the same reaction conditions were applied to the cyclization of 4, but only very low conversion (∼20%) was observed.
  • 43
    • 33947673321 scopus 로고    scopus 로고
    • For an alternative synthesis, leading to the jerangolid D C1-C6 fragment, see:
    • For an alternative synthesis, leading to the jerangolid D C1-C6 fragment, see:. Pospíšil J., and Markó I.E. J. Am. Chem. Soc. 129 (2007) 3516-3517
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 3516-3517
    • Pospíšil, J.1    Markó, I.E.2
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    • note
    • 23a


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.