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Volumn 76, Issue 6, 2011, Pages 1605-1613

Concise enantiospecific, stereoselective syntheses of (+)-Crispine A and Its (-)-antipode

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION REACTIONS; ENANTIOPURE; ENANTIOSPECIFIC; ISOLATED YIELD; NATURAL PRODUCTS; PROPANOATE; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; TOTAL SYNTHESIS; TWO-STEP PROTOCOL;

EID: 79953885697     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102112k     Document Type: Article
Times cited : (33)

References (99)
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    • 0036558479 scopus 로고    scopus 로고
    • For the most recent reviews, see:
    • For the most recent reviews, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
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    • Scott, J.D.1    Williams, R.M.2
  • 41
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    • This is the general case in which the intermediate iminium salt is linear (i.e., not cyclic), allowing the adoption of the (E)-configuration in the chairlike transition state. For examples, see:
    • This is the general case in which the intermediate iminium salt is linear (i.e., not cyclic), allowing the adoption of the (E)-configuration in the chairlike transition state. For examples, see: (a) Yamada, S.; Konda, M.; Shioiri, T. Tetrahedron Lett. 1972, 22, 2215.
    • (1972) Tetrahedron Lett. , vol.22 , pp. 2215
    • Yamada, S.1    Konda, M.2    Shioiri, T.3
  • 59
    • 0024467787 scopus 로고
    • On the other hand, substrates that generate a cyclic intermediate iminium salt (e.g., arising from precursors where the amine moiety is tethered to the aldehyde) force the adoption of the (Z)-configuration in the transition state, leading to a preference for the formation of 1,3-trans products. For examples, see:
    • (a) On the other hand, substrates that generate a cyclic intermediate iminium salt (e.g., arising from precursors where the amine moiety is tethered to the aldehyde) force the adoption of the (Z)-configuration in the transition state, leading to a preference for the formation of 1,3-trans products. For examples, see: (a) Tomioka, K.; Kubota, Y.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1622.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 1622
    • Tomioka, K.1    Kubota, Y.2    Koga, K.3
  • 70
    • 0028213944 scopus 로고
    • Although precursor (S)-(+)-2a was predicted to ultimately provide the opposite absolute configuration of naturally occurring crispine A, it was much less expensive and more readily available than the enantiomeric D-DOPA-derived building block (R)-(-)-2a for carrying out our efforts.
    • Although precursor (S)-(+)-2a was predicted to ultimately provide the opposite absolute configuration of naturally occurring crispine A, it was much less expensive and more readily available than the enantiomeric D-DOPA-derived building block (R)-(-)-2a for carrying out our efforts.(a) Tsuda, Y.; Hosoi, S.; Ishida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 204
    • Tsuda, Y.1    Hosoi, S.2    Ishida, K.3    Sangai, M.4
  • 73
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    • Variation in size for the reported cases in which the phenethylamine R-substituents affect the stereochemical outcome for 1,3-disubstituted tetrahydroisoquinolines have been limited to cases where the intermediate iminium species is cyclic (see ref 13). This effect for 1,3-disubstituted tetrahydro-ß-carbolines has been well-studied: see ref 10 and
    • Variation in size for the reported cases in which the phenethylamine R-substituents affect the stereochemical outcome for 1,3-disubstituted tetrahydroisoquinolines have been limited to cases where the intermediate iminium species is cyclic (see ref 13). This effect for 1,3-disubstituted tetrahydro-ß-carbolines has been well-studied: see ref 10 and Van Linn, M. L.; Cook, J. M. J. Org. Chem. 2010, 75, 3587.
    • (2010) J. Org. Chem. , vol.75 , pp. 3587
    • Van Linn, M.L.1    Cook, J.M.2
  • 85
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    • The tactic of using a natural chiral amino acid or derivative as a template for induced asymmetry in a carbon-carbon bond forming reaction to prepare amine heterocycles, followed by excision of the R-functionality by decarboxylation through a selenyl ester intermediate, is a strategy that has found similar utility. For examples, see ref 20c and 21d and
    • The tactic of using a natural chiral amino acid or derivative as a template for induced asymmetry in a carbon-carbon bond forming reaction to prepare amine heterocycles, followed by excision of the R-functionality by decarboxylation through a selenyl ester intermediate, is a strategy that has found similar utility. For examples, see ref 20c and 21d and (a) Martin, S. F.; Chen, K. X.; Eary, C. T. Org. Lett. 1999, 1, 79.
    • (1999) Org. Lett. , vol.1 , pp. 79
    • Martin, S.F.1    Chen, K.X.2    Eary, C.T.3
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    • Although precursor (S)-(+)-13 was predicted to ultimately provide the opposite absolute configuration of naturally-occurring crispine A, it was much less expensive and more readily available than the enantiomeric D-DOPAderived building block (R)-(-)-14 for carrying out our efforts
    • Schöllkopf, S. Tetrahedron 1983, 39, 2085. Although precursor (S)-(+)-13 was predicted to ultimately provide the opposite absolute configuration of naturally-occurring crispine A, it was much less expensive and more readily available than the enantiomeric D-DOPAderived building block (R)-(-)-14 for carrying out our efforts.
    • (1983) Tetrahedron , vol.39 , pp. 2085
    • Schöllkopf, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.