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Volumn 6, Issue 20, 2004, Pages 3637-3640

Spongistatin synthetic studies. Evolution of a scalable synthesis for the EF fragment of (+)-spongistatin 1 exploiting a petasis-ferrier union/rearrangement tactic

Author keywords

[No Author keywords available]

Indexed keywords

SPONGISTATIN 1;

EID: 6444227497     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048418f     Document Type: Article
Times cited : (38)

References (47)
  • 8
    • 6444225900 scopus 로고    scopus 로고
    • note
    • See refs 8-11 for a list of synthetic studies towards the spongistatins.
  • 26
    • 6444233368 scopus 로고    scopus 로고
    • note
    • Prepared in two steps exploiting Evans oxazolidinone chemistry; see the Supporting Information.
  • 27
    • 6444239282 scopus 로고    scopus 로고
    • note
    • Upon scale-up, TfOH (≃9 mol %) was added, as the reaction does not proceed otherwise, suggesting that adventitious water was more pronounced on small scale thereby generating TfOH in situ.
  • 29
    • 6444222933 scopus 로고    scopus 로고
    • note
    • The stereochemistry in (-)-11 was established on the basis of NOEs observed between the C(39), C(40), and C(43) hydrogens.
  • 31
    • 6444238606 scopus 로고    scopus 로고
    • note
    • Silylation at C(42) served to minimize chelation-control in the reduction, which otherwise resulted in poor selectivity.
  • 35
    • 33947085552 scopus 로고
    • The C(38) stereochemistry was confirmed by Mosher ester analysis; see: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 512
    • Dale, J.A.1    Mosher, H.S.2
  • 36
    • 2142858450 scopus 로고
    • The C(38) stereochemistry was confirmed by Mosher ester analysis; see: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 40
    • 6444228630 scopus 로고    scopus 로고
    • note
    • This is in the 1,5-syn sense, opposite to 1,5-anti stereoinduction observed for boron aldol reactions of simple β-alkoxy ketones, suggesting in this case, the overwhelming contribution from the more remote stereocenters; see ref 9.
  • 41
    • 0000275815 scopus 로고
    • 2; see: (a) Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286. (b) Evans, D. A.; Truesdale, L. K. J. Chem. Soc., Chem. Commun. 1973, 55.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 5286
    • Stork, G.1    Maldonado, L.2
  • 43
    • 6444226572 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for the preparation of 24.
  • 45
    • 6444221368 scopus 로고    scopus 로고
    • note
    • The C(47) stereochemistry was confirmed by chemical correlation to an intermediate prepared in our previous synthesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.