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Volumn 64, Issue 17, 2008, Pages 3713-3735

Studies towards complex bridged alkaloids: regio- and stereocontrolled enolate chemistry of 2,5-diketopiperazines

Author keywords

Cationic cyclisation; Diketopiperazine; Paraherquamide; Stephacidin

Indexed keywords

1,4 BIS(4 METHOXYBENZYL) 3 BENZYL 6 BENZYLIDENEPIPERAZINE 2,5 DIONE; 1,4 BIS(4 METHOXYBENZYL) 3 METHYL 6 METHYLENEPIPERAZINE 2,5 DIONE; 1,4 BIS(4 METHOXYBENZYL) 3,3,6 TRIMETHYLPIPERAZINE 2,5 DIONE; 1,4 BIS(4 METHOXYBENZYL) 3,6 DIBENZYL 3 HYDROXYLPHENYLMETHYLPIPERAZINE 2,5 DIONE; 1,4 BIS(4 METHOXYBENZYL) 3,6 DIMETHYL 3 PHENYLSULFANYLPIPERAZINE 2,5 DIONE; 2 (4 METHOXYBENZYL) 3 METHYL 8A (3 METHYLBUT 2 ENYL)OCTAHYDROPYRROLO[1,2A]PYRAZINE 1,4 DIONE; 3 ALLYL 1,4 BIS(4 METHOXYBENZYL) 3,6 DIMETHYLPIPERAZINE 2,5 DIONE; 3 ALLYL 3,6 DIBENZYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3 ALLYL 3,6 DIBENZYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE RAC; 3 BENZYL 1,4 BIS(4 METHOXYBENZYL) 3,6 DIMETHYLPIPERAZINE 2,5 DIONE; 3 BENZYL 3,6 DIETHYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3 CARBOETHOXY 1,4 BIS(4 METHOXYBENZYL) 3,6 DIMETHYLPIPERAZINE 2,5 DIONE; 3 CARBOETHOXY 3,6 DIBENZYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3 ETHYL 1,4 BIS(4 METHOXYBENZYL) 3,6 DIMETHYLPIPERAZINE 2,5 DIONE; 3,6 DIALLYL 1,4 BIS(4 METHOXYBENZYL)3 PHENYLSULFANYLPIPERAZINE 2,5 DIONE RAC; 3,6 DIALLYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3,6 DIALLYL 3 BENZYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE RAC; 3,6 DIALLYL 3 ETHYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE RAC; 3,6 DIBENZYL 1,4 BIS(4 METHOXYBENZYL) 3 PHENYLSULFANYLPIPERAZINE 2,5 DIONE RAC; 3,6 DIBENZYL 1,4 BIS(4 METHOXYBENZYL)3 PHENYLSULFANYLPIPERAZINE 2,5 DIONE RAC; 3,6 DIBENZYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3,6 DIBENZYL 3 ETHYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3,6 DIBENZYL 3 ETHYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE RAC; 3,6 DIETHYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 3,6 DIISOPROPYL 1,4 BIS(4 METHOXYBENZYL)PIPERAZINE 2,5 DIONE; 8A ALLYL 2 (4 METHOXYBENZYL) 3 METHYL OCTAHYDROPYRROLO[1,2A]PYRAZINE 1,4 DIONE; 8A ALLYL 3 BENZYL 2 (4 METHOXYBENZYL)OCTAHYDROPYRROLO[1,2A]PYRAZINE 1,4 DIONE; 8A ALLYL 3 ISOPROPYL 2 (4 METHOXYBENZYL)OCTAHYDROPYRROLO[1,2A]PYRAZINE 1,4 DIONE; PIPERAZINEDIONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 40649086596     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.020     Document Type: Article
Times cited : (28)

References (87)
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    • Recent synthesis:
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    • As far as we are aware there are no examples of desymmetrisation of centrosymmetric substrates by deprotonation.
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    • (a) For a review of chiral lithium amide base reactions, see: P. O'Brien J. Chem. Soc., Perkin Trans. 1 1998 1439 For our most recent papers, see:
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    • See:
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    • In some previous chiral base work we established that LiCl was crucial for high levels of asymmetric induction, see:
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    • Our DKP synthesis follows along known lines, see for example:
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    • See Ref.  2 for reviews. For isolation and biological activity, synthesis, and biosynthesis of paraherquamides, see inter alia:
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    • For key biosynthetic papers, see Refs. 2 and 17c,d . See also:
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    • Closure of an indole onto the methylvinyl appendage of a preformed bridged DKP features in many of the syntheses cited above. Our synthesis design was inspired by a very early paper from the Williams group, see: R.M. Williams T. Glinka Tetrahedron Lett. 27 1986 3581
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    • (b) See also Y. Ishida T. Aida J. Am. Chem. Soc. 124 2002 14017 For enolisation–substitution of cyclo(Pro, Pro), see:
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14017
    • Ishida, Y.1    Aida, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.