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Volumn 74, Issue 5, 2009, Pages 2008-2012

Stereoselective synthesis of (-)-spicigerolide

Author keywords

[No Author keywords available]

Indexed keywords

RING-CLOSING METATHESIS; SIGMATROPIC REARRANGEMENTS; STEREO-SELECTIVE SYNTHESIS; STEREOSELECTIVE ADDITIONS;

EID: 64249088241     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025753     Document Type: Article
Times cited : (26)

References (40)
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    • Falomir, E.; Murga, J.; Ruiz, P.; Carda, M.; Marco, J. A.; Pereda-Miranda, R.; Fragoso-Serrano, M.; Cerda-Garc?́a-Rojas, C. M. J. Org. Chem. 2003, 68, 5672-5676.
    • (c) Falomir, E.; Murga, J.; Ruiz, P.; Carda, M.; Marco, J. A.; Pereda-Miranda, R.; Fragoso-Serrano, M.; Cerda-Garc?́a-Rojas, C. M. J. Org. Chem. 2003, 68, 5672-5676.
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    • Alemany, A.; Márquez, C.; Pascual, C.; Valverde, S.; Perales, A.; Fayos, J.; Mart?́nez-Ripoll, M. Tetrahedron Lett. 1979, 37, 3583-3586.
    • (b) Alemany, A.; Márquez, C.; Pascual, C.; Valverde, S.; Perales, A.; Fayos, J.; Mart?́nez-Ripoll, M. Tetrahedron Lett. 1979, 37, 3583-3586.
  • 11
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    • The structure of synargentolideAhas been questioned recently: Garc?́a-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Arkivoc 2005, ix, 175-188.
    • The structure of synargentolideAhas been questioned recently: Garc?́a-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Arkivoc 2005, ix, 175-188.
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    • Murga, J.; Garc?́a-Fortanet, J.; Carda, M.; Marco, J. A. Tetrahedron Lett. 2003, 44, 1737-1739.
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    • (b) Garc?́a-Fortanet, J.; Murga, J.; Carda, M.; Marco, J. A. Tetrahedron 2004, 60, 12261-12267.
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  • 23
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    • For reviews on stereoselective approaches to these αβ- unsaturated δ-lactones, see: a
    • For reviews on stereoselective approaches to these αβ- unsaturated δ-lactones, see: (a) Boucard, V.; Broustal, G.; Campagne, J.-M. Eur. J. Org. Chem. 2007, 225-236.
    • (2007) Eur. J. Org. Chem , pp. 225-236
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  • 27
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    • For the use of allylic esters in Carreira's alkynylations, see: a
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    • (2001) Org. Lett , vol.3 , pp. 3017-3020
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  • 30
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    • However, addition in the presence of (+)-NME led to the opposite configuration of the new stereocenter (90:10 dr), showing that stereoselectivity is ruled by either the (+) or (-)-NME used. As reported in ref 13a, the influence of the configuration of the silicon-protected lactaldehyde on the stereochemistry of the addition is low when an achiral ligand was used.
    • However, addition in the presence of (+)-NME led to the opposite configuration of the new stereocenter (90:10 dr), showing that stereoselectivity is ruled by either the (+) or (-)-NME used. As reported in ref 13a, the influence of the configuration of the silicon-protected lactaldehyde on the stereochemistry of the addition is low when an achiral ligand was used.
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    • The relative stereochemistry of syn and anti adducts was confirmed by comparison of the spectral data following the analysis in Kojima, N.; Maezaki, N.; Tominaga, H.; Asai, M.; Yanai, M.; Tanaka, T. Chem. Eur. J. 2003, 9, 4980-4990.
    • The relative stereochemistry of syn and anti adducts was confirmed by comparison of the spectral data following the analysis in Kojima, N.; Maezaki, N.; Tominaga, H.; Asai, M.; Yanai, M.; Tanaka, T. Chem. Eur. J. 2003, 9, 4980-4990.
  • 32
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    • 2, and amine base should be increased to improve the yields and enantioselectivities in some reluctant substrates was first reported by Boyal, D.; López, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
    • 2, and amine base should be increased to improve the yields and enantioselectivities in some reluctant substrates was first reported by Boyal, D.; López, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.