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Volumn 65, Issue 5, 2009, Pages 1048-1058

Efficient synthesis of syringolides, secosyrins, and syributins through a common approach

Author keywords

[No Author keywords available]

Indexed keywords

ARABINOSE; BUTENOLIDE; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; KETONE; NATURAL PRODUCT; SECOSYRIN 1; SECOSYRIN 2; SESQUITERPENE DERIVATIVE; SYRIBUTIN 1; SYRIBUTIN 2; SYRINGOLIDE 1; SYRINGOLIDE 2; UNCLASSIFIED DRUG;

EID: 57649199706     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.079     Document Type: Article
Times cited : (17)

References (74)
  • 6
    • 57649194069 scopus 로고    scopus 로고
    • Selected recent publications:
    • Selected recent publications:
  • 36
    • 57649163181 scopus 로고    scopus 로고
    • note
    • Refs. 8, 12, 14a, 19a.
  • 43
    • 57649173204 scopus 로고    scopus 로고
    • Preliminary results of this work were presented in:
    • Preliminary results of this work were presented in:
  • 44
    • 57649173202 scopus 로고    scopus 로고
    • 1st European Chemistry Congress, Budapest, Hungary, August 2006, p 329 (N-PO-94);
    • 1st European Chemistry Congress, Budapest, Hungary, August 2006, p 329 (N-PO-94);
  • 45
    • 57649168035 scopus 로고    scopus 로고
    • 2nd Hellenic Symposium on Organic Synthesis, Athens, Greece, April 2007, p 53 (L17).
    • 2nd Hellenic Symposium on Organic Synthesis, Athens, Greece, April 2007, p 53 (L17).
  • 48
    • 57649207174 scopus 로고    scopus 로고
    • Intermediates 10 and 11 have been previously prepared from d-mannitol, following a different synthetic scheme:
    • Intermediates 10 and 11 have been previously prepared from d-mannitol, following a different synthetic scheme:
  • 51
    • 57649157008 scopus 로고    scopus 로고
    • note
    • Sugar numbering.
  • 54
    • 57649141541 scopus 로고    scopus 로고
    • note
    • Using NaH and t-BuOK as bases resulted in the formation of these esters in almost the same ratios but in much lower yields.
  • 55
    • 57649212630 scopus 로고    scopus 로고
    • note
    • As expected the ratio of Z/E isomers remained the same (ca. 4:1).
  • 56
    • 57649197056 scopus 로고    scopus 로고
    • note
    • Structural assignment was based on NOE studies, which revealed the indicated crucial effects (see Scheme 3).
  • 57
    • 57649150886 scopus 로고    scopus 로고
    • note
    • Only slow decomposition of starting material was observed.
  • 58
    • 57649173203 scopus 로고    scopus 로고
    • note
    • Obviously, the bulkiness of the TBDPS group played a decisive role regarding the inactivity of these substrates.
  • 62
    • 57649160198 scopus 로고    scopus 로고
    • note
    • Analogous conclusions could be reached by examining the opened formed intermediates (erythro and threo).
  • 64
    • 57649163179 scopus 로고    scopus 로고
    • note
    • These compounds were found to have identical physical and spectra data with those reported in the literature.
  • 65
    • 57649141542 scopus 로고    scopus 로고
    • note
    • The 3-O-TBS derivative instead of 3-O-benzyl one (21).
  • 66
    • 57649157006 scopus 로고    scopus 로고
    • note
    • 3, DME were used.
  • 67
    • 57649173201 scopus 로고    scopus 로고
    • note
    • It was observed that ketone 18 slowly decomposes, even when stored at -20 °C, giving lactol 23.
  • 69
    • 57649173200 scopus 로고    scopus 로고
    • note
    • This approach gave directly 1a and 1b in good overall yields (45-55%) only when 4-5 mg scale experiments were employed. Using bigger quantities of starting material resulted in an unexplained dramatic drop of the yields. Commercially available TMSI or the in situ generated one (from TMSCl and NaI) was employed.
  • 70
    • 57649168034 scopus 로고    scopus 로고
    • note
    • 2O was used as solvent.
  • 71
    • 57649212629 scopus 로고    scopus 로고
    • note
    • No tetrahydrofuran-type product was found after careful investigation of the reaction mixture.
  • 73
    • 57649197054 scopus 로고    scopus 로고
    • note
    • A simultaneous debenzylation (see Ref. 8b) did not occur.
  • 74
    • 57649204005 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra and LC-MS analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.