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Volumn 8, Issue 20, 2006, Pages 4477-4480

Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BRYOSTATIN; BRYOSTATIN 7; MACROLIDE;

EID: 33750037020     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061626i     Document Type: Article
Times cited : (72)

References (43)
  • 2
    • 0001399971 scopus 로고
    • For reviews on bryostatin chemistry and biology, see: (a) Norcross, R.; Paterson, I. Chem. Rev. 1995, 95, 2041.
    • (1995) Chem. Rev. , vol.95 , pp. 2041
    • Norcross, R.1    Paterson, I.2
  • 6
    • 0010051744 scopus 로고    scopus 로고
    • Fusetani, N., Ed.; Karger: Basel
    • Mendola, D. In Drugs from the Sea; Fusetani, N., Ed.; Karger: Basel, 2000; p 20.
    • (2000) Drugs from the Sea , pp. 20
    • Mendola, D.1
  • 23
    • 33646448125 scopus 로고    scopus 로고
    • and the references therein
    • (b) Wender, P. A.; Verma, V. A. Org. Lett. 2006, 8, 1893 and the references therein.
    • (2006) Org. Lett. , vol.8 , pp. 1893
    • Wender, P.A.1    Verma, V.A.2
  • 24
    • 0035932595 scopus 로고    scopus 로고
    • For other dithiane alkylation strategies for constructing the C(9)-C(10) bond of the bryostatins, see: (a) Vakalopoulos, A.; Lampe, T. F. J.; Hoffmann, H. M. R. Org. Lett. 2001, 3, 929.
    • (2001) Org. Lett. , vol.3 , pp. 929
    • Vakalopoulos, A.1    Lampe, T.F.J.2    Hoffmann, H.M.R.3
  • 25
    • 33750041550 scopus 로고    scopus 로고
    • Ref 9
    • (b) Ref 9.
  • 28
    • 33750039546 scopus 로고    scopus 로고
    • note
    • (c) Generally, we have found it more convenient and far less sacrificial to conduct this C-methylation with ketone 9 that has only been recrystallized twice. Generally, two recrystallizations provide material that is approximately 90% pure; the other main contaminant appears to be 1-phenylpentan-2-ol.
  • 31
    • 33750035079 scopus 로고    scopus 로고
    • note
    • 3 reagent with the anomeric OMe would also favor delivery of hydride to the underside of 8 to give 15, but a referee has argued against this proposal on the basis that, if it did occur, it would most likely cause loss of the acid-labile C(9)-OMe.
  • 42
    • 33750080941 scopus 로고    scopus 로고
    • ref 2c
    • (f) For earlier work, see: ref 2c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.