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Volumn 11, Issue 9, 2009, Pages 1891-1894

Biomimetic synthesis of tangutorine following new biogenetic proposals

Author keywords

[No Author keywords available]

Indexed keywords

CARBOLINE DERIVATIVE; INDOLE ALKALOID; QUINOLIZINE DERIVATIVE; TANGUTORINE;

EID: 65549170002     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9002916     Document Type: Article
Times cited : (28)

References (30)
  • 9
    • 66149115711 scopus 로고    scopus 로고
    • Using the classical biogenetic numbering proposed by Le Men and Taylor which has the advantage of showing the structural homogeneity within the apparent diversity of these alkaloids
    • Using the classical "biogenetic" numbering proposed by Le Men and Taylor which has the advantage of showing the structural homogeneity within the apparent diversity of these alkaloids.
  • 10
    • 66149134152 scopus 로고    scopus 로고
    • With the exception of nitraraine which structure is questioned. An extensive survey on Nitraria alkaloids will soon be disclosed elsewhere as a review article
    • With the exception of nitraraine which structure is questioned. An extensive survey on Nitraria alkaloids will soon be disclosed elsewhere as a review article.
  • 18
    • 66149087801 scopus 로고    scopus 로고
    • This is of particular interest in terms of chemotaxonomy. The two families are not related to one another
    • This is of particular interest in terms of chemotaxonomy. The two families are not related to one another.
  • 21
    • 33751500609 scopus 로고    scopus 로고
    • Compound 10 was reported before, it was characterized, at this time, as its perfluorobenzylhydroxylamine adduct. See: Tashima, T.; Imai, M.; Kuroda, Y.; Yagi, S.; Nakagawa, T. J. Org. Chem. 1991, 56, 694-697. No yield of the reaction was provided.
    • Compound 10 was reported before, it was characterized, at this time, as its perfluorobenzylhydroxylamine adduct. See: Tashima, T.; Imai, M.; Kuroda, Y.; Yagi, S.; Nakagawa, T. J. Org. Chem. 1991, 56, 694-697. No yield of the reaction was provided.
  • 22
    • 66149151490 scopus 로고    scopus 로고
    • The yield is obviously low and could easily constitute a major drawback of the synthesis, but experimentally speaking, glutaraldehyde 5 is a cheap reagent and 10 is the most apolar compound of the reaction based on silica gel TLC profile which renders its purification by chomatog- raphy easy. In practise, 15 g of 5 give 3-4gof 10 in a reproducible manner. We will give a full account of the other compounds isolated in due course, but 5, as suspected, mainly gives complex polymers.
    • The yield is obviously low and could easily constitute a major drawback of the synthesis, but experimentally speaking, glutaraldehyde 5 is a cheap reagent and 10 is the most apolar compound of the reaction based on silica gel TLC profile which renders its purification by chomatog- raphy easy. In practise, 15 g of 5 give 3-4gof 10 in a reproducible manner. We will give a full account of the other compounds isolated in due course, but 5, as suspected, mainly gives complex polymers.
  • 23
    • 66149098280 scopus 로고    scopus 로고
    • This intermediate is putative and the pathway depicted is one among others. The treatment of 10 in the same conditions but without tryptamine did not allow the isolation of 7 10 remained mostly unchanged and was partly converted into O-acetyl-10
    • This intermediate is putative and the pathway depicted is one among others. The treatment of 10 in the same conditions but without tryptamine did not allow the isolation of 7 (10 remained mostly unchanged and was partly converted into O-acetyl-10).
  • 24
    • 66149105224 scopus 로고    scopus 로고
    • Which could be isolated as a single diastereomer by recrystallization of a trifluoroacetate salt precipitated from H2.O/CH3CN 8:2
    • 3CN (8:2).
  • 25
    • 66149148404 scopus 로고    scopus 로고
    • See Supporting Information. Data were in agreement with the extensive analysis reported in R. P. Hsung's work (ref 4).
    • See Supporting Information. Data were in agreement with the extensive analysis reported in R. P. Hsung's work (ref 4).
  • 26
    • 66149155924 scopus 로고    scopus 로고
    • Analytical conditions, see Supporting Information, could not be transposed to preparative HPLC due to solubility/precipitation issues
    • Analytical conditions, see Supporting Information, could not be transposed to preparative HPLC due to solubility/precipitation issues.
  • 27
    • 66149112226 scopus 로고    scopus 로고
    • As exemplified, here, by the fact that 1 is isolated as an optically inactive compound as it is the case for a large majority of Nitraria alkaloids with the exception of simple spiro-alkaloids such as nitramine. For a recent discussion on the impact of spontaneity in the biosynthesis of natural products, see: Poupon, E.; Gravel, E. Eur. J. Org. Chem. 2008, 27-42.
    • As exemplified, here, by the fact that 1 is isolated as an optically inactive compound as it is the case for a large majority of Nitraria alkaloids with the exception of simple spiro-alkaloids such as nitramine. For a recent discussion on the impact of spontaneity in the biosynthesis of natural products, see: Poupon, E.; Gravel, E. Eur. J. Org. Chem. 2008, 27-42.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.