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Volumn 2007, Issue 4, 2007, Pages 206-219

C-10b Functionalized 5,6-dihydropyrrolo[2,1-a]isoquinolines as intermediates in the synthesis of erythrinane systems. Intra- vs. intermolecular conjugate addition based strategies

Author keywords

Conjugate addition; Erythrinanes; Functionalized organolithium compounds; Pyrroloisoquinolines; Ring closing metathesis

Indexed keywords


EID: 33846062814     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.418     Document Type: Article
Times cited : (8)

References (70)
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    • Pyrroloisoquinoline 11 has been previously prepared by allyl-lithium addition followed by N-acyliminium cylization with TFA see ref 3c, However, as stated there, by this route it is difficult to obtain the product in pure form due to contamination with the stannane residue of the precursor of the allyllithium. Besides, allylmagnesium chloride addition followed by α-amidoalkylation with TFA, BF3.OEt2 or TiCl4 did not give 11. In this case, allyl group is not stable under these conditions, and isomerization of the double bond occurs
    • 4 did not give 11. In this case, allyl group is not stable under these conditions, and isomerization of the double bond occurs.
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    • 1H decoupling experiments confirmed the stereochemistry of 12. For instance, an enhancement of the H-2 signals was observed upon irradiation on one of the methylene hydrogens of the allyl group in C-1 and vice versa. This fact, together with the absence of NOE between both allyl groups confirms they are in a trans disposition. The rest of the NOE experiments carried out were fully consistent with the proposed stereochemistry.
    • 1H decoupling experiments confirmed the stereochemistry of 12. For instance, an enhancement of the H-2 signals was observed upon irradiation on one of the methylene hydrogens of the allyl group in C-1 and vice versa. This fact, together with the absence of NOE between both allyl groups confirms they are in a trans disposition. The rest of the NOE experiments carried out were fully consistent with the proposed stereochemistry.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.