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Volumn 14, Issue 15, 2003, Pages 2277-2290

Lead tetraacetate mediated domino reactions on (R)-(-)-carvone-derived bicyclic unsaturated 1,2-diols and further rearrangements

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CARVONE; LEAD TETRAACETATE; ORGANOLEAD COMPOUND; UNCLASSIFIED DRUG;

EID: 0041698087     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00480-4     Document Type: Article
Times cited : (7)

References (29)
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    • (R)-(-)-carvone, a readily available monoterpene, is widely used as building block in the synthesis of natural products. Ho, T.-L., Enantioselective Synthesis of Natural Products from Chiral Terpenes, John-Wiley: Chichester, 1992
    • Swartz, H. J.; Verstegen-Haaksma, A.; Jansen, B. J. M.; de Groot, A. Tetrahedron 1994, 50, 10083-10094. (R)-(-)-carvone, a readily available monoterpene, is widely used as building block in the synthesis of natural products. Ho, T.-L., Enantioselective Synthesis of Natural Products from Chiral Terpenes, John-Wiley: Chichester, 1992.
    • (1994) Tetrahedron , vol.50 , pp. 10083-10094
    • Swartz, H.J.1    Verstegen-Haaksma, A.2    Jansen, B.J.M.3    De Groot, A.4
  • 14
    • 85031131936 scopus 로고    scopus 로고
    • Indeed, the domino transformations in acetic acid can be carried out directly on the bis-TMS protected diols 19. On the other hand, during several runs, substantial deprotection of the TMS groups was observed during Wittig olefination
    • Indeed, the domino transformations in acetic acid can be carried out directly on the bis-TMS protected diols 19. On the other hand, during several runs, substantial deprotection of the TMS groups was observed during Wittig olefination.
  • 15
    • 85031136029 scopus 로고    scopus 로고
    • The reason for not isolating the bis-lactyl analogue of 6 is that mixed acetals are present and their chromatographic separation (which is useless for further elaboration) is tedious
    • The reason for not isolating the bis-lactyl analogue of 6 is that mixed acetals are present and their chromatographic separation (which is useless for further elaboration) is tedious.
  • 16
    • 85031131180 scopus 로고    scopus 로고
    • Although as much as seven bond making-braking processes take place in one synthetic operation, the average yield is calculated based on only four transformations (oxidative/pericyclic/oxyplumbation/ring expansion)
    • Although as much as seven bond making-braking processes take place in one synthetic operation, the average yield is calculated based on only four transformations (oxidative/pericyclic/oxyplumbation/ring expansion).
  • 20
    • 85178444387 scopus 로고
    • Criegee R. Ber. 64:1931;260.
    • (1931) Ber. , vol.64 , pp. 260
    • Criegee, R.1
  • 23
    • 0344541866 scopus 로고    scopus 로고
    • We applied this chemistry to 'half-cascade' intermediates obtained from unsaturated bicyclic diols in the octaline-diol series as well as from steroidal diols: (a) Arseniyadis, S.; Quilez del Moral, J.; Brondi Alves, R.; Potier, P.; Toupet, L. Tetrahedron: Asymmetry 1998, 9, 2871-2878; (b) Rico Ferreira, M.; Martín Hernando, J. I.; Candela Lena, J. I.; Quílez del Moral, J.; Arseniyadis, S. Tetrahedron: Asymmetry 1999, 10, 1527-1537.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2871-2878
    • Arseniyadis, S.1    Quilez del Moral, J.2    Brondi Alves, R.3    Potier, P.4    Toupet, L.5
  • 24
    • 0033597429 scopus 로고    scopus 로고
    • We applied this chemistry to 'half-cascade' intermediates obtained from unsaturated bicyclic diols in the octaline-diol series as well as from steroidal diols: (a) Arseniyadis, S.; Quilez del Moral, J.; Brondi Alves, R.; Potier, P.; Toupet, L. Tetrahedron: Asymmetry 1998, 9, 2871-2878; (b) Rico Ferreira, M.; Martín Hernando, J. I.; Candela Lena, J. I.; Quílez del Moral, J.; Arseniyadis, S. Tetrahedron: Asymmetry 1999, 10, 1527-1537.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 1527-1537
    • Rico Ferreira, M.1    Martín Hernando, J.I.2    Candela Lena, J.I.3    Quílez Del Moral, J.4    Arseniyadis, S.5
  • 25
    • 0035906796 scopus 로고    scopus 로고
    • A number of possibilities exist for an efficient use of these chiral templates:
    • A number of possibilities exist for an efficient use of these chiral templates: Sarvary I., Almqvist F., Frejd T.L. Chem. Eur. J. 7:2001;2158-2166.
    • (2001) Chem. Eur. J. , vol.7 , pp. 2158-2166
    • Sarvary, I.1    Almqvist, F.2    Frejd, T.L.3
  • 26
    • 84918118498 scopus 로고
    • 2 mediated oxidation of 1,2-diols, known long ago, is a clean method for the cleavage of glycols:
    • 2 mediated oxidation of 1,2-diols, known long ago, is a clean method for the cleavage of glycols: Criegee R., Beucker H. Ann. Chem. 541:1939;218.
    • (1939) Ann. Chem. , vol.541 , pp. 218
    • Criegee, R.1    Beucker, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.