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Volumn 66, Issue 26, 2010, Pages 4745-4759

Total synthesis of (+)-papulacandin D

Author keywords

Asymmetric allylation; C Arylglycosides; Silicon based cross coupling

Indexed keywords

AROMATIC COMPOUND; GERANIOL; GLYCOPYRANOSIDE; GLYCOSIDE; IODIDE; LEWIS BASE; ORGANOSILICON DERIVATIVE; PALLADIUM; PAPULACANDIN D; PAPULACANDIN DERIVATIVE; POLYUNSATURATED FATTY ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77954242151     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.093     Document Type: Article
Times cited : (70)

References (158)
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    • Isolation:
    • Isolation:
  • 3
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    • Structural characterization:
    • Structural characterization:
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    • For L-687, 781 see:
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    • For Mer-WF3010 see:
    • For Mer-WF3010 see:
  • 24
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    • For BU-4794F see:
    • For BU-4794F see:
  • 26
    • 77954244149 scopus 로고    scopus 로고
    • For Saricandin see:
    • For Saricandin see:
  • 28
    • 77954241928 scopus 로고    scopus 로고
    • For chaetiacandin see:
    • For chaetiacandin see:
  • 31
    • 77954243220 scopus 로고    scopus 로고
    • For F-10748 A1, A2, B1,B2, C1, C2, D1, and D2 see:
    • For F-10748 A1, A2, B1,B2, C1, C2, D1, and D2 see:
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    • 77954244866 scopus 로고    scopus 로고
    • For arylglycoside synthesis see:
    • For arylglycoside synthesis see:
  • 52
    • 77954243630 scopus 로고    scopus 로고
    • For the total synthesis of papulacandin D see:
    • For the total synthesis of papulacandin D see:
  • 66
    • 77954244148 scopus 로고    scopus 로고
    • See Supplementary data for the synthesis of 9.
    • See Supplementary data for the synthesis of 9.
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    • C. Jäkel, and K.H. Dötz J. Organomet. Chem. 624 2001 172 185 Although the glycal actonide can be prepared from glucose via triacetyl glycal, but is low yielding
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  • 73
    • 77954244381 scopus 로고    scopus 로고
    • Direct formation of silanol from metalation of glucals and trapping with hexamethylcyclotrisiloxane the yields and scale were irreproducible.
    • Direct formation of silanol from metalation of glucals and trapping with hexamethylcyclotrisiloxane the yields and scale were irreproducible.
  • 76
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    • For the preparation of protected aromatic iodides see Supplementary data.
    • For the preparation of protected aromatic iodides see Supplementary data.
  • 80
    • 77954245024 scopus 로고    scopus 로고
    • It was found through deuterium incorporation experiments 1.0-1.5 equiv t-BuLi was sufficient to effect the lithiation at C(1), see Supplementary data.
    • It was found through deuterium incorporation experiments 1.0-1.5 equiv t-BuLi was sufficient to effect the lithiation at C(1), see Supplementary data.
  • 82
    • 77954243297 scopus 로고    scopus 로고
    • Attempts to trap C(1)-lithio 41 with dichlorodimethylsilane, followed by hydrolysis of the corresponding chlorosilane, under pH 5.0 buffered aqueous conditions, gave disiloxane as the sole product.
    • Attempts to trap C(1)-lithio 41 with dichlorodimethylsilane, followed by hydrolysis of the corresponding chlorosilane, under pH 5.0 buffered aqueous conditions, gave disiloxane as the sole product.
  • 83
    • 77954243016 scopus 로고    scopus 로고
    • This type of nonoxidative spiroketalization was observed with 57 in the presence of acidic media.
    • This type of nonoxidative spiroketalization was observed with 57 in the presence of acidic media.
  • 84
    • 77954244012 scopus 로고    scopus 로고
    • The 82% yield was consistently reproducible on both 1.0-5.0 mmol scales.
    • The 82% yield was consistently reproducible on both 1.0-5.0 mmol scales.
  • 88
    • 77954243601 scopus 로고    scopus 로고
    • TMS/ethanol:
    • TMS/ethanol:
  • 90
    • 77954242451 scopus 로고    scopus 로고
    • SEM-Cl:
    • SEM-Cl:
  • 96
    • 77954242907 scopus 로고    scopus 로고
    • Grubbs' second-generation catalysts: (1,3-bis-(2,4,6-trimethylphenyl)-2- imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium.
    • Grubbs' second-generation catalysts: (1,3-bis-(2,4,6-trimethylphenyl)-2- imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium.
  • 107
    • 77954243362 scopus 로고    scopus 로고
    • Salt free conditions:
    • Salt free conditions:
  • 111
    • 77954241993 scopus 로고    scopus 로고
    • Commercially available geraniol was enriched by spinning band distillation (GC analysis 99.8% geraniol/0.2% nerol)
    • Commercially available geraniol was enriched by spinning band distillation (GC analysis 99.8% geraniol/0.2% nerol)
  • 116
    • 77954243326 scopus 로고    scopus 로고
    • See Supplementary data for a complete list of chemical shift data.
    • See Supplementary data for a complete list of chemical shift data.
  • 118
    • 77954244950 scopus 로고    scopus 로고
    • Removal of SEM from alcohols: CsF, HMPA:
    • Removal of SEM from alcohols: CsF, HMPA:
  • 120
    • 77954244505 scopus 로고    scopus 로고
    • TFA
    • TFA..:
  • 122
    • 77954244848 scopus 로고    scopus 로고
    • Ammonium flouride sources in HMPA or THF:
    • Ammonium flouride sources in HMPA or THF:
  • 124
    • 77954242433 scopus 로고    scopus 로고
    • TBAF, MS4 and, DMPU:
    • TBAF, MS4, DMPU:
  • 126
    • 77954241867 scopus 로고    scopus 로고
    • 2O:
    • 2O:
  • 128
    • 77954242628 scopus 로고    scopus 로고
    • 2O:
    • 2O:
  • 130
    • 77954242643 scopus 로고    scopus 로고
    • 2O:
    • 2O:
  • 132
    • 77954243195 scopus 로고    scopus 로고
    • 2:
    • 2:
  • 134
    • 77954242840 scopus 로고    scopus 로고
    • 2O:
    • 2O:
  • 136
    • 77954242283 scopus 로고    scopus 로고
    • SEM deprotection from phenol:
    • SEM deprotection from phenol:
  • 138
    • 77954244628 scopus 로고    scopus 로고
    • 4:
    • 4:
  • 140
    • 77954242096 scopus 로고    scopus 로고
    • 4:
    • 4:
  • 142
    • 77954242700 scopus 로고    scopus 로고
    • TBAF, MS4 and, DMPU:
    • TBAF, MS4, DMPU:
  • 144
    • 77954242390 scopus 로고    scopus 로고
    • HCl
    • HCl,.:
  • 146
    • 77954242085 scopus 로고    scopus 로고
    • Anhydrous TBAF:
    • Anhydrous TBAF:
  • 148
    • 77954244345 scopus 로고    scopus 로고
    • 3CN:
    • 3CN:
  • 150
    • 77954243829 scopus 로고    scopus 로고
    • 2, hν:
    • 2, hν:
  • 152
    • 77954241937 scopus 로고    scopus 로고
    • Preparation of trialkylsilyloxymethyl chlorides:
    • Preparation of trialkylsilyloxymethyl chlorides:
  • 156
    • 77954242721 scopus 로고    scopus 로고
    • See Supplementary data for the preparation of the buffered HF solutions.
    • See Supplementary data for the preparation of the buffered HF solutions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.