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Volumn 69, Issue 25, 2004, Pages 8810-8820

Total synthesis of ustiloxin D and considerations on the origin of selectivity of the asymmetric allylic alkylation

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 10044222144     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048854f     Document Type: Article
Times cited : (37)

References (60)
  • 22
    • 10044243311 scopus 로고    scopus 로고
    • Ph.D. Thesis, Stanford University, Stanford, California; Chapters 2 and 3
    • (d) Woiwode, T. F. Ph.D. Thesis, Stanford University, Stanford, California, 2000; Chapters 2 and 3.
    • (2000)
    • Woiwode, T.F.1
  • 27
    • 10044253999 scopus 로고    scopus 로고
    • note
    • SEM: 2-(trimethylsilyl)ethoxymethyl.
  • 34
    • 10044249595 scopus 로고    scopus 로고
    • note
    • As measured by analytical HPLC using a Chiralpak AD chiral column.
  • 35
    • 0042379988 scopus 로고    scopus 로고
    • and references contained therein
    • Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943 and references contained therein.
    • (2003) Chem. Rev. , vol.103 , pp. 2921-2943
    • Trost, B.M.1    Crawley, M.L.2
  • 37
    • 0028097524 scopus 로고
    • Similar difficulties with hydrolysis of an ester with an α-N-methylated carbamate were observed by: Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8544-8556
    • Boger, D.L.1    Patane, M.A.2    Zhou, J.3
  • 43
    • 10044295725 scopus 로고    scopus 로고
    • note
    • TEMPO: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical.
  • 45
    • 10044224152 scopus 로고    scopus 로고
    • note
    • BOP: benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate.
  • 47
    • 10044292598 scopus 로고    scopus 로고
    • note
    • DMPU: 1,3-dimethyl-3,4,5,6-tetrahydro-2(H)-pyrimidinone.
  • 52
    • 10044284997 scopus 로고    scopus 로고
    • note
    • HATU: O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate.
  • 53
    • 10044221582 scopus 로고    scopus 로고
    • note
    • BEP: 1-ethyl-2-bromopyrdinium tetrafluoroborate.
  • 55
    • 10044259337 scopus 로고    scopus 로고
    • note
    • As detailed in Supporting Information for ref 14.
  • 58
    • 0037019541 scopus 로고    scopus 로고
    • Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. 2002, 124, 10396-10415
    • (c) Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. 2002, 124, 10396-10415.
  • 59
    • 10044258422 scopus 로고    scopus 로고
    • note
    • We have attributed the discrepancy in ust D 1:C2-epi ust D 80 using (R,R) 81 and (S,S) 24 ligands to reaction diastereoselectivity for each of the two isomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.