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Volumn 62, Issue 18, 2006, Pages 4349-4354

Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from d-glucose

Author keywords

Alkaloids; Azasugars; Wittig olefination

Indexed keywords

1,2 DIHYDROXYPYRROLIZIDINE; 1,2 EPILENTIGINOSINE; BENZYLAMINE DERIVATIVE; ESTER; ESTER DERIVATIVE; GLUCOSE; INDOLIZIDINE ALKALOID; LACTONE DERIVATIVE; LENTIGINOSINE; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE ALKALOID; UNCLASSIFIED DRUG;

EID: 33646106115     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.074     Document Type: Article
Times cited : (32)

References (35)
  • 5
    • 33646115125 scopus 로고    scopus 로고
    • note
    • D +0.19 and +3.2, respectively. The synthesis of both enantiomers of lentiginosine was reported by Gurjar et al., starting from (R) and (S)-pipecolinic acid and showed that the (-)-lentiginosine has the all R stereochemistry. However, the subsequent report of Brandi et al. claim that natural lentiginosine is not levorotatory but dextrorotatory and this has the (1S,2S,8aS) configuration.
  • 27
    • 0033533589 scopus 로고    scopus 로고
    • (a) d-Glucose derived α,β-unsaturated ester was utilized by us in the synthesis of azasugars see: (a)
    • (a) d-Glucose derived α,β-unsaturated ester was utilized by us in the synthesis of azasugars see: (a). Desai V.N., Saha N.N., and Dhavale D.D. J. Chem. Soc., Chem. Commun. (1999) 1719
    • (1999) J. Chem. Soc., Chem. Commun. , pp. 1719
    • Desai, V.N.1    Saha, N.N.2    Dhavale, D.D.3
  • 33
    • 33646107102 scopus 로고    scopus 로고
    • note
    • This is an unpublished work from our laboratory. For details see: Chiron approaches to polyhydroxylated pyrrolidine, indolizidine, pyrrolizidine alkaloids and sphingolipids, Chaudhari, V. D. Ph. D. dissertation, University of Pune, October 2005.
  • 34
    • 33646097409 scopus 로고    scopus 로고
    • note
    • Reaction of γ-lactone 6b with DIBAL-H afforded corresponding lactol, which on the Wittig olefination led to the formation of inseparable diastereomeric mixture of unexpected conjugate addition adduct X.{A figure is presented}


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.