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Volumn 60, Issue 43 SPEC. ISS., 2004, Pages 9569-9588

Enantioselective total synthesis of (-)-strychnine: Development of a highly practical catalytic asymmetric carbon-carbon bond formation and domino cyclization

Author keywords

( ) Strychnine; Catalytic asymmetric Michael reaction; Domino cyclization; Enantioselective total synthesis

Indexed keywords

ALKENE; CARBON; IMINE; LEWIS ACID; STRYCHNINE;

EID: 4544269722     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.141     Document Type: Conference Paper
Times cited : (53)

References (117)
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    • Although we initially used the term 'tandem cyclization' for the reaction shown in Scheme 9 (Ref. 9), we use herein 'domino cyclization' based on Prof. Tietze's suggestion. See Ref. 34.
    • Although we initially used the term 'tandem cyclization' for the reaction shown in Scheme 9 (Ref. 9), we use herein 'domino cyclization' based on Prof. Tietze's suggestion. See Ref. 34.
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    • * interaction.
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    • When EtOH was used as a solvent, the reaction proceeded very fast with low selectivity (62: 64 =∼1:1). On the other hand, MeOH had low reactivity (half conversion even with large reagent excess) and high selectivity (62: 64 =>50:1).
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    • The spectroscopic data for synthetic 65 and 1 matched those reported previously, see Section 4.
    • The spectroscopic data for synthetic 65 and 1 matched those reported previously, see Section 4.
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    • 2, 0°C to rt for 12 h. The obtained product was purified by distillation (76-78°C/4 mm Hg). The two-step yield of amination and domino cyclization was highly dependent on the purity of the thioacetal.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.