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Volumn 52, Issue 17, 2011, Pages 2080-2084

Enantioselective formal total synthesis of the Dendrobatidae frog toxin, (+)-pumiliotoxin B, via O-directed alkyne free radical hydrostannation

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; FREE RADICAL; PUMILIOTOXIN; PUMILIOTOXIN B; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79953207291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.141     Document Type: Article
Times cited : (22)

References (28)
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    • For our detailed investigations into the mechanism of the O-directed alkylacetylene hydrostannation
    • For our detailed investigations into the mechanism of the O-directed alkylacetylene hydrostannation, see: Dimopoulos, P.; George, J.; Manaviazar, S.; Tocher, D. A.; Hale, K. J. Org. Lett. 2005, 7, 5377-5380.
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    • Dimopoulos, P.1    George, J.2    Manaviazar, S.3    Tocher, D.A.4    Hale, K.J.5
  • 4
    • 77953202408 scopus 로고    scopus 로고
    • For an account of our attempts to use this stannation method in the synthesis of the A83586C/kettapeptin pyran side-chain
    • For an account of our attempts to use this stannation method in the synthesis of the A83586C/kettapeptin pyran side-chain, see: Hale, K. J.; Manaviazar, S.; George, J. Chem. Commun. 2010, 46, 4021-4042.
    • (2010) Chem. Commun. , vol.46 , pp. 4021-4042
    • Hale, K.J.1    Manaviazar, S.2    George, J.3
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    • (1967) Science , vol.156 , pp. 970-973
    • Daly, J.W.1    Myers, C.W.2
  • 7
    • 0021172960 scopus 로고
    • For previous (+)-pumiliotoxin B total syntheses, (a)
    • For previous (+)-pumiliotoxin B total syntheses, see: (a) Overman, L. E.; Bell, K. L.; Ito, F. J. Am. Chem. Soc. 1984, 4192-4201;
    • (1984) J. Am. Chem. Soc. , pp. 4192-4201
    • Overman, L.E.1    Bell, K.L.2    Ito, F.3
  • 10
    • 0037047553 scopus 로고    scopus 로고
    • For a review on pumiliotoxin alkaloid synthesis
    • (d) Aoyagi, S.; Hirashima, S.; Saito, K.; Kibayashi, C. J. Org. Chem. 2002, 67, 5517-5526; For a review on pumiliotoxin alkaloid synthesis, see:
    • (2002) J. Org. Chem. , vol.67 , pp. 5517-5526
    • Aoyagi, S.1    Hirashima, S.2    Saito, K.3    Kibayashi, C.4
  • 12
    • 0021131561 scopus 로고
    • For recent syntheses of the structurally related allo-pumiliotoxins
    • For recent syntheses of the structurally related allo-pumiliotoxins, see: (a) Overman, L. E.; Goldstein, S. W. J. Am. Chem. Soc. 1984, 106, 5360-5361;
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5360-5361
    • Overman, L.E.1    Goldstein, S.W.2
  • 19
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    • Eneyne asymmetric dihydroxylation: (a) For the AD procedure
    • Eneyne asymmetric dihydroxylation: (a) Jeong, K.-S.; Sjo, P.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 3833-3836; For the AD procedure, see:
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3833-3836
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    • For a related stereocontrolled iodohydroxylation on the N-benzoyl-pyrrolidine analogue of 11 This example proceeded with 10:1 stereoselectivity in favour of the desired tertiary alcohol-iodide, but unfortunately, difficulties were subsequently encountered in the removal of the N-benzoyl group. A priori, we considered that use of an N-trifluoroacetamide might overcome these difficulties and give rise to an identical stereochemical outcome, and lead to 10 with good stereocontrol
    • For a related stereocontrolled iodohydroxylation on the N-benzoyl-pyrrolidine analogue of 11 see: Overman, L. E. McCready, R. J. Tetrahedron Lett. 1982, 23, 4887. This example proceeded with 10:1 stereoselectivity in favour of the desired tertiary alcohol-iodide, but unfortunately, difficulties were subsequently encountered in the removal of the N-benzoyl group. A priori, we considered that use of an N-trifluoroacetamide might overcome these difficulties and give rise to an identical stereochemical outcome, and lead to 10 with good stereocontrol.
    • (1982) J. Tetrahedron Lett. , vol.23 , pp. 4887
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    • 3N Swern-type oxidation, we now have good reason to suspect that the latter process may have epimerized the C(11)-centre before the alkynylation was effected. Our future full account will look into this step again
    • 3N Swern-type oxidation, we now have good reason to suspect that the latter process may have epimerized the C(11)-centre before the alkynylation was effected. Our future full account will look into this step again.
    • (1994) Synlett , pp. 107-108
    • Miwa, K.1    Aoyama, T.2    Shioiri, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.