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Volumn 13, Issue 2, 2011, Pages 347-349

Concise and protective group-free syntheses of (±)-hamigeran B and (±)-4-bromohamigeran B

Author keywords

[No Author keywords available]

Indexed keywords

4 BROMOHAMIGERAN B; 4-BROMOHAMIGERAN B; HAMIGERAN B; NAPHTHOQUINONE;

EID: 78651486697     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102780s     Document Type: Article
Times cited : (35)

References (34)
  • 8
    • 15944425033 scopus 로고    scopus 로고
    • For a review of pre-2005 syntheses, see
    • For a review of pre-2005 syntheses, see: Clive, D. L. J.; Wang, J. Org. Prep. Proc. Int. 2005, 37, 1
    • (2005) Org. Prep. Proc. Int. , vol.37 , pp. 1
    • Clive, D.L.J.1    Wang, J.2
  • 13
    • 78651518251 scopus 로고    scopus 로고
    • For approaches to hamigeran B, see
    • For approaches to hamigeran B, see
  • 17
    • 0010399912 scopus 로고
    • Enone 5 had been previously reported as a minor byproduct
    • Enone 5 had been previously reported as a minor byproduct: Attah-Poku, S. K.; Chau, F.; Yadav, V. K.; Fallis, A. G. J. Org. Chem. 1985, 50, 3418
    • (1985) J. Org. Chem. , vol.50 , pp. 3418
    • Attah-Poku, S.K.1    Chau, F.2    Yadav, V.K.3    Fallis, A.G.4
  • 22
    • 0001295005 scopus 로고
    • For a similar application, see
    • For a similar application, see: Paquette, L. A.; Wang, X. J. Org. Chem. 1994, 59, 2052
    • (1994) J. Org. Chem. , vol.59 , pp. 2052
    • Paquette, L.A.1    Wang, X.2
  • 24
    • 78651495820 scopus 로고    scopus 로고
    • Each of the intermediates 10 and 12 were used in the following transformation without purification and were not fully characterized. All other compounds were isolated, purified, and exhibited spectra in accord with assigned structures and gave satifactory elemental analyses or molecular mass determinations
    • Each of the intermediates 10 and 12 were used in the following transformation without purification and were not fully characterized. All other compounds were isolated, purified, and exhibited spectra in accord with assigned structures and gave satifactory elemental analyses or molecular mass determinations.
  • 25
    • 78651510628 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 30
    • 78651480166 scopus 로고    scopus 로고
    • 1H NMR. As the stereochemistry of the newly formed stereogenic centers of 16 were to be destroyed through subsequent aromatization, no attempt was made to determine their configuration
    • 1H NMR. As the stereochemistry of the newly formed stereogenic centers of 16 were to be destroyed through subsequent aromatization, no attempt was made to determine their configuration.
  • 31
    • 78651481331 scopus 로고    scopus 로고
    • Note that the use of the acetal functionality in 13 was to both activate the diene and to provide the enol functionality in the cyclized product. Consequently, the ketal formed in 16 as a result of the Diels-Alder cyclization does not actually serve as a protective group
    • Note that the use of the acetal functionality in 13 was to both activate the diene and to provide the enol functionality in the cyclized product. Consequently, the ketal formed in 16 as a result of the Diels-Alder cyclization does not actually serve as a protective group.
  • 33
    • 0003043082 scopus 로고
    • For a review, see
    • For a review, see: Rabjohn, N. Org. React. 1976, 24, 261
    • (1976) Org. React. , vol.24 , pp. 261
    • Rabjohn, N.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.