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Volumn 76, Issue 10, 2011, Pages 3684-3690

Application of the helquist annulation in lycopodium alkaloid synthesis: Unified total syntheses of (-)-8-deoxyserratinine, (+)-fawcettimine, and (+)-lycoflexine

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROXYLATION; KEY FEATURE; MANNICH CYCLIZATION; N-ALKYLATION; NINE-MEMBERED RINGS; SHI EPOXIDATION; TOTAL SYNTHESIS;

EID: 79956071522     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1023188     Document Type: Article
Times cited : (48)

References (46)
  • 1
    • 66149189158 scopus 로고    scopus 로고
    • For recent reviews of the Lycopodium alkaloids
    • For recent reviews of the Lycopodium alkaloids, see Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679-729
    • (2009) Heterocycles , vol.77 , pp. 679-729
    • Hirasawa, Y.1    Kobayashi, J.2    Morita, H.3
  • 3
    • 77954644732 scopus 로고    scopus 로고
    • For selected recent total syntheses of Lycopodium alkaloids
    • For selected recent total syntheses of Lycopodium alkaloids, see Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594-9595
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 9594-9595
    • Liau, B.B.1    Shair, M.D.2
  • 31
    • 79956152585 scopus 로고    scopus 로고
    • 2) as an efficient nitrogen nucleophile for synthesis of medium- or large-sized cyclic amines
    • 2) as an efficient nitrogen nucleophile for synthesis of medium- or large-sized cyclic amines.
  • 34
    • 79956101450 scopus 로고    scopus 로고
    • note
    • 2 was finally chosen not only because it can give the best yield but also because it can be readily deprotected into the free amine 1, leaving the other functionalities of the substrate untouched.
  • 35
    • 79956100933 scopus 로고    scopus 로고
    • Similar conditions used by the Heathcock group in their fawcettimine total synthesis. See ref 5b
    • Similar conditions used by the Heathcock group in their fawcettimine total synthesis. See ref 5b.
  • 36
    • 79956098839 scopus 로고    scopus 로고
    • The ratio of undesired α isomer to desired β is high, up to 2:1
    • The ratio of undesired α isomer to desired β is high, up to 2:1.
  • 40
    • 79956090066 scopus 로고    scopus 로고
    • 3 failed to give the products
    • 3 failed to give the products.
  • 43
    • 79956150481 scopus 로고    scopus 로고
    • D +89 (c 0.55, MeOH)
    • D +89 (c 0.55, MeOH).
  • 44
    • 77958035710 scopus 로고    scopus 로고
    • During the early stage of preparation of this manuscript, one elegant synthesis of lycoflexine has been published by Mulzer et al.: Ramharter, J.; Weinstabl, H.; Mulzer, J. J. Am. Chem. Soc. 2010, 132, 14338-14339. Mulzer used similar conditions as Ayer did, namely, acidic aqueous HCHO in extended reaction time (48 h) employed to accomplish this important biomimetic transformation. The first asymmetric total synthesis of lycoflexine including the assignment of the absolute configuration was reported by the Mulzer group.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 14338-14339
    • Ramharter, J.1    Weinstabl, H.2    Mulzer, J.3
  • 45
    • 0015527097 scopus 로고
    • A similar protocol adopted by the Evans group in their total synthesis of the Lycopodium alkaloid luciduline; see
    • A similar protocol adopted by the Evans group in their total synthesis of the Lycopodium alkaloid luciduline; see Scott, W. L.; Evans, D. A. J. Am. Chem. Soc. 1972, 94, 4779-4780
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 4779-4780
    • Scott, W.L.1    Evans, D.A.2
  • 46
    • 79956097514 scopus 로고    scopus 로고
    • note
    • D +5.0 (c 0.42, DCM).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.