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Volumn 72, Issue 24, 2007, Pages 9314-9322

Diastereoselective construction of quaternary carbons directed via macrocyclic ring conformation: Formal synthesis of (-)-mesembrine

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE CONSTRUCTION; MACROCYCLIC RING CONFORMATION; QUATERNARY CARBONS;

EID: 36649030118     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701833v     Document Type: Article
Times cited : (34)

References (86)
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    • Pioneering work of Still demonstrated that the conformation of medium and large macrocycles affords an effective vehicle in which the asymmetric synthesis of stereogenic centers can be achieved. See: (a) Still, W. C, Galynker, I. Tetrahedron 1981, 37, 3981
    • Pioneering work of Still demonstrated that the conformation of medium and large macrocycles affords an effective vehicle in which the asymmetric synthesis of stereogenic centers can be achieved. See: (a) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981.
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    • The relative configuration of 10 was established without ambiguity by COSY and NOESY experiments. See the Supporting Information.
    • The relative configuration of 10 was established without ambiguity by COSY and NOESY experiments. See the Supporting Information.
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    • For an ORTEP view of 11, see the Supporting Information.
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    • Other electrophiles such as aldehydes and α,β-unsaturated aldehydes or ketones were found to be unreactive under these reaction conditions
    • Other electrophiles such as aldehydes and α,β-unsaturated aldehydes or ketones were found to be unreactive under these reaction conditions.
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    • The oxy-Cope reaction of 26 proved to be a reversible process. In fact, submission of 27 to the reaction condition gave back the same ratio of 26 and 27.
    • The oxy-Cope reaction of 26 proved to be a reversible process. In fact, submission of 27 to the reaction condition gave back the same ratio of 26 and 27.
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    • Vinyl bromide 36 was easily prepared from commercially available 3,4-dimethoxybenzaldehyde in three steps. See: (a) Rosiak, A.; Christoffers, J. Synlett 2006, 1434.
    • Vinyl bromide 36 was easily prepared from commercially available 3,4-dimethoxybenzaldehyde in three steps. See: (a) Rosiak, A.; Christoffers, J. Synlett 2006, 1434.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.