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Volumn 63, Issue 41, 2007, Pages 10211-10225

A synthetic strategy using Witkop's pyrroloindole for (-)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B

Author keywords

[No Author keywords available]

Indexed keywords

(2,3A) 1 ACETYL 3A (3 METHYL 2 BUTENYL) 2 METHOXYCARBONYL 1,2,3,3A TETRAHYDROPYRROLO[2,3B]INDOLE; (2,3A) 8 ACETYL 3A (3 METHYL 2 BUTENYL) 2 METHOXYCARBONYL 2,3,3A,8 TETRAHYDROPYRROLO[2,3B]INDOLE; (2,3A) 8 METHYL 3A (3 METHYL 2 BUTENYL) 2 METHOXYCARBONYL 2,3,3A,8 TETRAHYDROPYRROLO[2,3B]INDOLE; (2,3A)1 ACETYL 3A (3 METHYL 2 BUTENYL)2 METHOXYCARBONYL 1,2,3,3A TETRAHYDROPYRROLO[2,3 B]INDOLE; (3A,8A) 3A,8 BIS(3 METHYL 2 BUTENYL) 3,3A,8,8A TETRAHYDROPYRROLO[2,3 B]INDOLE; (3A,8A) 3A,8 BIS(3 METHYL 2 BUTENYL)3,3A,8,8A TETRAHYDROPYRROLO[2,3 B]INDOLE; 1,3 BIS(3 METHYL 2 BUTENYL) 1H INDOLE; INDOLE DERIVATIVE; PRENYLAMINE; TRYPTOPHAN; UNCLASSIFIED DRUG;

EID: 34548306948     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.091     Document Type: Article
Times cited : (22)

References (51)
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    • Such an approach involving a Claisen rearrangement of an oxindole derivative for syntheses of (-)-flustramines and (-)-flustramides has been reported, see:
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    • note
    • Interestingly exposure of 21b to a solution of NaOMe/MeOH (2 M, 6.10 mmol) containing hydrazine (0.51 mmol) for a day, at rt, also gave 30b in a comparable yield (39%).
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    • 2 as the solvent, the ion pair is likely to have more covalent character. If some electrostatic attraction between the bulky cation and the ester group is invoked (Fig. 3), then the β-face becomes more shielded and diastereoselection during alkylation becomes possible. Such an attraction, among other factors, is believed to be important in explaining the origin of the enantioselectivity in the alkylation of prochiral ketones catalysed by chiral quaternary salts of Cinchona alkaloids. For the mechanism of chiral induction, see:. Ojima I. (Ed), Wiley-VCH, New York, NY pp 585, 736
    • 2 as the solvent, the ion pair is likely to have more covalent character. If some electrostatic attraction between the bulky cation and the ester group is invoked (Fig. 3), then the β-face becomes more shielded and diastereoselection during alkylation becomes possible. Such an attraction, among other factors, is believed to be important in explaining the origin of the enantioselectivity in the alkylation of prochiral ketones catalysed by chiral quaternary salts of Cinchona alkaloids. For the mechanism of chiral induction, see:. In: Ojima I. (Ed). Chiral Asymmetric Synthesis (2000), Wiley-VCH, New York, NY pp 585, 736
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    • 3 species. For examples of such reactions, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.