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Volumn 60, Issue 34, 2004, Pages 7301-7314

Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis

Author keywords

Diastereoselective reduction; Enantioselective synthesis; Iminium ion; Pyrrolidine; Ring closing metathesis

Indexed keywords

ALKADIENE; ANATOXIN A; CHOLINERGIC RECEPTOR STIMULATING AGENT; DEXTRO METHYLPYROGLUTAMATE; PYROGLUTAMIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 3343008747     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.021     Document Type: Conference Paper
Times cited : (87)

References (76)
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    • For a recent review of applications of RCM to the synthesis of oxygen and nitrogen heterocycles, see:
    • For a recent review of applications of RCM to the synthesis of oxygen and nitrogen heterocycles, see: Deiters A., Martin S.F. Chem. Rev. 104:2004;2199-2238
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    • For a review of earlier syntheses of
    • For a review of earlier syntheses of 1 see: (a) Mansell H.L. Tetrahedron. 52:1996;6025-6061
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    • For a preliminary account of some of this work, see:
    • For a preliminary account of some of this work, see: Brenneman J.B., Martin S.F. Org. Lett. 6:2004;1329-1331
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    • Subsequent to publication of our synthesis of
    • Subsequent to publication of our synthesis of 1 (Ref. 14), another synthesis has been published in which an enyne RCM was used to construct the bicyclic ring system. See: Mori M., Tomita T., Kita Y., Kitamura T. Tetrahedron Lett. 45:2004;4397-4399
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4397-4399
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    • The synthesis of the closely related alkaloid (-)-ferruginine using an enyne RCM to construct the requisite azabicyclo[3.2.1]octane skeleton was recently reported. See:
    • The synthesis of the closely related alkaloid (-)-ferruginine using an enyne RCM to construct the requisite azabicyclo[3.2.1]octane skeleton was recently reported. See: Aggarwal V.K., Astle C.J., Rogers-Evans M. Org. Lett. 6:2004;1469-1471
    • (2004) Org. Lett. , vol.6 , pp. 1469-1471
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    • 2, 65°C
    • 2, 65°C
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    • Subsequent to these studies, a successful Wacker oxidation on a related azabicyclic intermediate was reported. See Ref. 16
    • Subsequent to these studies, a successful Wacker oxidation on a related azabicyclic intermediate was reported. See Ref. 16
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    • For the addition of organometallic nucleophiles to N-alkoxycarbonyl lactams, see: (a)
    • For the addition of organometallic nucleophiles to N-alkoxycarbonyl lactams, see: (a) Ohta T., Hosoi A., Kimura T., Nozoe S. Chem. Lett. 1987;2091-2094
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    • We thank Professor G. B. Dudley for providing us with details prior to publication
    • Sunderhaus J.D., Lam H., Dudley G.B. Org. Lett. 5:2003;4571-4573. We thank Professor G. B. Dudley for providing us with details prior to publication
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    • note
    • The diastereoselectivy was determined by GC analysis using a Hewlett Packard 5890 Series II instrument fitted with an Alltech ECONO-CAP SE-54 column (initial Temp=110°C, final Temp 200°C at 5°C/min; retention time=17.1 min for 15 and 21.4 min for 18)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.