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Volumn 2, Issue 16, 2000, Pages 2467-2470

Total synthesis of cristatic acid

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CRISTATIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; SALICYLIC ACID DERIVATIVE;

EID: 0034632402     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061236     Document Type: Article
Times cited : (52)

References (46)
  • 3
    • 0001048203 scopus 로고
    • See the following for leading references on studies towards related farnesyl phenol natural products; some of them further illustrate the difficulties arising in the final deprotection steps of the aryl ether groups: (a) Chen, K.-M.; Semple, J. E.; Joullié, M. M. J. Org. Chem. 1985, 50, 3997.
    • (1985) J. Org. Chem. , vol.50 , pp. 3997
    • Chen, K.-M.1    Semple, J.E.2    Joullié, M.M.3
  • 16
    • 85037504234 scopus 로고    scopus 로고
    • note
    • Silyl ethers instead of SEM groups were ruled out for the reason given in ref 19.
  • 18
    • 85037515475 scopus 로고    scopus 로고
    • note
    • For details see the Supporting Information.
  • 26
    • 0039697372 scopus 로고
    • 2O, rt, 77%) in analogy to a procedure described in: Garner, P.; Park, J. M. Synth. Commun. 1987, 17, 189.
    • (1987) Synth. Commun. , vol.17 , pp. 189
    • Garner, P.1    Park, J.M.2
  • 31
    • 85037516397 scopus 로고    scopus 로고
    • note
    • Compounds 10-12 are obtained as mixtures of stereoisomers. Since all of them converge into product 13, the synthesis depicted in Scheme 2 was carried out with these mixtures and no attempts were made to isolate the individual isomers.
  • 33
    • 85037518330 scopus 로고    scopus 로고
    • note
    • (b) At this point it is essential to have chosen a PMB group rather than a simple Bn ether as the protecting group for the benzylic alcohol. All attempts to cleave the corresponding benzyl ether failed to afford the desired product 14. For example, attempted hydrogenation over Pd/C reduces the furan ring without cleaving the benzyl ether.
  • 35
    • 85037521481 scopus 로고    scopus 로고
    • note
    • Note that attempted alkylations of the metalated sulfone with an allyl bromide analogous to 7 carrying -OTBDMS instead of -OSEM groups gave the desired compound in less than 5% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.