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Volumn 45, Issue 34, 2004, Pages 6407-6411

An enantioselective synthesis of phomopsolide D

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBON; FURAN DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE; PHOMOPSOLIDE D; UNCLASSIFIED DRUG;

EID: 4143112330     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.011     Document Type: Article
Times cited : (51)

References (20)
  • 6
    • 0035940146 scopus 로고    scopus 로고
    • For the synthesis of cryptocarya diacetate see: T.J. Hunter, and G.A. O'Doherty Org. Lett. 3 17 2001 2777 2780
    • (2001) Org. Lett. , vol.3 , Issue.17 , pp. 2777-2780
    • Hunter, T.J.1    O'Doherty, G.A.2
  • 8
    • 0035844707 scopus 로고    scopus 로고
    • For the application of this approach toward several styryllactone natural products see: J.M. Harris, and G.A. O'Doherty Tetrahedron 57 2001 5161 5171
    • (2001) Tetrahedron , vol.57 , pp. 5161-5171
    • Harris, J.M.1    O'Doherty, G.A.2
  • 10
    • 4143143690 scopus 로고    scopus 로고
    • note
    • Noshita's route to phomopsolide B required 24 steps and our own route to phomopsolide C required 12 steps from furfural and 4 steps to prepare Wittig reagent 4
  • 12
    • 4143151216 scopus 로고    scopus 로고
    • note
    • 2 so the material was used as is
  • 14
    • 37649026044 scopus 로고    scopus 로고
    • Noyori has noted this tandem 1,4/1,2 reduction to be the minor product of the reduction of cyclohexanone, see: R. Noyori, and T. Ohkuma Angew. Chem., Int. Ed. 40 2001 40 73
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 40-73
    • Noyori1    Ohkuma, T.R.2
  • 15
    • 4143063110 scopus 로고    scopus 로고
    • note
    • At this stage Mosher ester analysis indicated that 11a/b were formed in >96% ee
  • 16
    • 0017494276 scopus 로고
    • An Achmatowicz reaction is the oxidative rearrangement of furfuryl alcohols to 2-substituted 6-hydroxy-2H-pyran-3(6H)-ones, see: O. Achmatowicz, and R. Bielski Carbohydr. Res. 55 1977 165 176
    • (1977) Carbohydr. Res. , vol.55 , pp. 165-176
    • Achmatowicz1    Bielski, R.O.2
  • 19
    • 4143096440 scopus 로고    scopus 로고
    • note
    • 3 was removed from the reaction conditions
  • 20
    • 4143068579 scopus 로고    scopus 로고
    • note
    • We found a significantly higher optical rotation for 1d than what was reported from the isolation work, Ref. 2. This is most likely a concentration effect (1.25 mg/mL as opposed to 0.0045 mg/mL)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.