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Volumn 70, Issue 21, 2005, Pages 8352-8363

New asymmetric approach to natural pyrrolizidines: Synthesis of (+)-amphorogynine A, (+)-amphorogynine D, and (+)-retronecine

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; SYNTHESIS (CHEMICAL);

EID: 26844514473     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050983o     Document Type: Article
Times cited : (42)

References (84)
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    • (1988) Pyrrolizidine Alkaloids
  • 19
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    • For a preliminary account of a portion of this work, see: Roche, C.; Delair, P.; Greene, A. E. Org. Lett. 2003, 5, 1741-1744.
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    • Roche, C.1    Delair, P.2    Greene, A.E.3
  • 61
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    • Because of the small crystal size (0.3 × 0.04 × 0.04 mm) and its weak diffraction, this analysis could only be achieved with the high-intensity, microfocused source at the European Synchrotron Radiation Facility (ID13 Microfocus Beamline). Diffraction patterns from crystals as small as 3 × 3 × <1 μm can be recorded and refined through the use of this unique tool. See: Gaillot, A. C.; Flot, D.; Drits, V. A.; Manceau, A.; Burghammer, M.; Lanson, B. Chem. Mater. 2003, 15, 4666-4678.
    • (2003) Chem. Mater. , vol.15 , pp. 4666-4678
    • Gaillot, A.C.1    Flot, D.2    Drits, V.A.3    Manceau, A.4    Burghammer, M.5    Lanson, B.6
  • 63
    • 26844532275 scopus 로고    scopus 로고
    • note
    • max range 2.04-29.10°, 117 141 measured reflections, 5949 LR(int) = 0.089] independent reflections, refinement on F: R(1) [1 > 2σ (I)] = 0.046, wR2 [all data] = 0.075, GOF (all data) = 1.969. The Cristallographic Information File (CIF) has been deposited at the Cambridge Crystallographic Data Centre, as CCDC 271614. These data can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax, (+44) 1223-336-033; deposit@ccdc.cam.ac.uk.
  • 76
    • 20444508149 scopus 로고    scopus 로고
    • Allylic alcohol 17 had recently been prepared in our laboratory in conjunction with another project. See: Ceccon, J.; Poisson, J.-F.; Greene, A. E. Synlett 2005, 1413-1416.
    • (2005) Synlett , pp. 1413-1416
    • Ceccon, J.1    Poisson, J.-F.2    Greene, A.E.3
  • 77
    • 0037185537 scopus 로고    scopus 로고
    • Several alternative methods were unsuccessful: Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845-866.
    • (2002) Tetrahedron , vol.58 , pp. 845-866
    • Andrus, M.B.1    Lashley, J.C.2
  • 80
    • 13344254217 scopus 로고
    • Bao, A. V. R.; Mysorekar, S. V.; Yadav, J. S. Synth. Commun. 1987, 17, 1339-1347. Uncatalyzed hydroboration with disiamylborane, borane-dimethyl sulfide, dihexylborane, or 9-BBN gave a low yield and/or unsatisfactory regioselectivity.
    • (1987) Synth. Commun. , vol.17 , pp. 1339-1347
    • Bao, A.V.R.1    Mysorekar, S.V.2    Yadav, J.S.3
  • 82
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    • Complex multiplets (m) have been analyzed, when possible, by using the method of Hoye and co-workers: Hoye, T. R.; Hanson, P. R.; Vyvyan, J. R. J. Org. Chem. 1994, 59, 4096-4103.
    • (1994) J. Org. Chem. , vol.59 , pp. 4096-4103
    • Hoye, T.R.1    Hanson, P.R.2    Vyvyan, J.R.3
  • 84
    • 0027879008 scopus 로고
    • 2) mounted on a translation rail, which in turn was mounted on a rotation arm. The rotation arm and φ-axis were aligned in order to be collinear. The crystal was embedded with a cryoprotectant (Paratone-N from Hampton) and then taken in a nylon loop (from Hampton Research). Several crystals were tested to select a single crystal of suitable quality for data collection. Two data sets were collected by the oscillation technique (the first, 100 frames, each with an exposure time of 2 s and 6° oscillation; the second, 100 frames, each with an exposure time of 2 s and 4° oscillation), using a two-dimensional CCD detector at 45 mm and with the cryoloop axis approximately parallel to the oscillation axis. To probe only a homogeneous part of the needle-shaped crystal, the focused beam was reduced to 30 μm in diameter by using a beam-defining aperture. The measurement was carried out at a fixed temperature of 100(2) K by using an Oxford Cryostream device. The frames were indexed and the reflections integrated using the XDS software suite (Kabsch, W. J. Appl. Crystallogr. 1993, 26, 795-800). Each reflection intensity was corrected for intensity loss due to air absorption. The two data sets were merged with XSCALE.
    • (1993) J. Appl. Crystallogr. , vol.26 , pp. 795-800
    • Kabsch, W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.