A directed metalation route to the zwitterionic indole alkaloids.

Gribble, Gordon W.; Barden, Timothy C.; Johnson, David A.

doi:10.1016/s0040-4020(01)85951-2

Cited by 47 publications

(28 citation statements)

References 25 publications

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“…[8][9][10][11][12][13][14][15][16]; δ H 2.88 (2H), t, J = 7.5 Hz, δ C 35.3 (CH 2 -17)]. These observations suggested that ring E in 11 was opened in 9/9a.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

Yang

Liao

et al. 2015

J. Nat. Prod.

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Nine new alkaloids of the koumine (1-4), humantenine (5-7), and yohimbane (8, 9) types as well as 12 known analogues were isolated from the leaves and vine stems of Gelsemium elegans. Compound 1 is the first N-4-demethyl alkaloid of the koumine type, compound 7 is the first nor-humantenine alkaloid, and compounds 8 and 9 are the first N-1-oxide and the first seco-E-ring alkaloids, respectively, of the yohimbane type. Compounds 1 and 7 exhibited moderate cytotoxicity against five human tumor cell lines with IC50 values in the range 4.6-9.3 μM.

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“…[8][9][10][11][12][13][14][15][16]; δ H 2.88 (2H), t, J = 7.5 Hz, δ C 35.3 (CH 2 -17)]. These observations suggested that ring E in 11 was opened in 9/9a.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

Yang

Liao

et al. 2015

J. Nat. Prod.

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“…CHE1039027) for funds to purchase the X-ray diffractometer. tionality using selenium dioxide (Gribble et al, 1988) in 60% yield. Similar Nazarov cyclizations with indoles (Bergman & Venemalm, 1992;Cheng & Cheung, 1996;Ishikura et al, 2000;Miki et al, 2001;Churruca et al, 2010) have been reported.…”

Section: Methodsmentioning

confidence: 99%

“…For examples of Nazarov cyclizations with indoles, see: Bergman & Venemalm (1992); Cheng & Cheung (1996); Ishikura et al (2000); Miki et al (2001); Churruca et al (2010). For examples of -diketone oxidations using selenium dioxide, see: Gribble et al (1988); Xu et al (2002); Belsey et al (2006). For related cyclopenta [b]indolone alkaloids and their analogues, see: Cheng et al (1991); Garcia-Pichel & Castenholz (1991); Garcia-Pichel et al (1992); Proteau et al (1993); Ekebergh et al (2011); Kobayashi et al (1994); Jacquemard et al (2004); Ploutno & Carmeli (2001).…”

Section: Related Literaturementioning

confidence: 99%

3,3-Dimethyl-1,2,3,4-tetrahydrocyclopenta[b]indole-1,2-dione (bruceolline E)

et al. 2012

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“…Several elegant syntheses have been reported, notably by Swan, 7 Westphal, 8 Potts, 9 and Gribble. 10 It has been targeted due to its antitumor activity, arising from topoisomerase 1 inhibition, DNA intercalation, and other mechanisms. 11 Routes to sempervirine generally involve moderately long synthetic sequences, proceed with a modest overall yield, and have limitations in scope for preparing the natural material or a small set of analogues.…”

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confidence: 99%