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Volumn 46, Issue 25, 2007, Pages 4693-4697

Total synthesis of (+)-azaspiracid-1. Part I: Synthesis of the fully elaborated ABCD aldehyde

Author keywords

Ene reaction; Natural products; Nucleophilic addition; Spiroketalization; Total synthesis

Indexed keywords

ALDEHYDES; ENANTIOSELECTIVITY; ENZYMES; NUCLEOPHILES; SULFONATION; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES;

EID: 34347245264     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701515     Document Type: Article
Times cited : (36)

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    • Abbreviations: Bn, benzyl, CBS, Corey-Bakshi-Shibata, DDQ, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, DMAP, 4-dimethylaminopyridine, DMF, N,N-dimethylformamide, DMP, Dess-Martin periodinane, DMSO, dimethylsulfoxide, LDA, lithium diisopropylamide, LiDBB, lithium di-tert-butyl biphenylide, Mes, 2,4,6-trimethylphenyl, Nu, nucleophile, PMB, 4-methoxybenzyl, PPTS, pyridinium p-toluenesulfonate, py, pyridine, TBAF, tetrabutylammonium fluoride, TBDPS, tert- butyldiphenylsilyl, TBS, tert-butyldimethylsilyl, TES, triethylsilyl, TIPS, triisopropylsilyl
    • Abbreviations: Bn = benzyl, CBS = Corey-Bakshi-Shibata, DDQ = 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, DMAP = 4-dimethylaminopyridine, DMF = N,N-dimethylformamide, DMP = Dess-Martin periodinane, DMSO = dimethylsulfoxide, LDA = lithium diisopropylamide, LiDBB = lithium di-tert-butyl biphenylide, Mes = 2,4,6-trimethylphenyl, Nu = nucleophile, PMB = 4-methoxybenzyl, PPTS = pyridinium p-toluenesulfonate, py = pyridine, TBAF = tetrabutylammonium fluoride, TBDPS = tert- butyldiphenylsilyl, TBS = tert-butyldimethylsilyl, TES = triethylsilyl, TIPS = triisopropylsilyl.
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    • The selective removal of the TES group was accompanied by minor loss of the TIPS protecting group at C1. Since the crude mixture of 33 was subjected directly to the PPTS-mediated spirocyclization, 76% of 34 was obtained directly in the spirocyclization event while an additional 7% of 34 was obtained after reinstallation of the TIPS substituent at C21
    • The selective removal of the TES group was accompanied by minor loss of the TIPS protecting group at C1. Since the crude mixture of 33 was subjected directly to the PPTS-mediated spirocyclization, 76% of 34 was obtained directly in the spirocyclization event while an additional 7% of 34 was obtained after reinstallation of the TIPS substituent at C21.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.