Syntheses of velbanamine and catharanthine

Buechi, George; Kulsa, Peter; Ogasawara, Kunio; Rosati, Robert L.

doi:10.1021/ja00707a043

Cited by 67 publications

(21 citation statements)

References 1 publication

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“…We chose alcohol 24 , in which each stereocenter is unequivocally defined, as the target compound (Scheme ). In their elegant total synthesis of (±)‐catharanthine, Büchi et al demonstrated that 24 could be transformed readily into catharanthine by introducing the methoxycarbonyl group at C16 and effecting dehydration of the tertiary alcohol 5a…”

Section: Methodsmentioning

confidence: 99%

Formal Synthesis of (+)‐Catharanthine

et al. 2006

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Madagascan periwinkle is the current source of (+)‐catharanthine, the crucial building block of the major antitumor agent vinorelbine. In the formal synthesis of this natural product, the key intermediate 1 described by Büchi and co‐workers was obtained in virtually optically pure form from L‐serine. The strategy presented may be viewed as a general synthetic approach to optically active isoquinuclidines.

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Section: Methodsmentioning

confidence: 99%

Formal Synthesis of (+)‐Catharanthine

et al. 2006

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“…Buchi's group described the synthesis of cleavamine in connection with the synthesis of catharanthine. 81 Isoquinuclidine was chosen as the starting material as it was used previously in the synthesis of iboga-alkaloids. 41 The unstable diketone 145 was reduced with excess NaBH 4 to give diol 146 as a major product which this was reduced to 147, a precursor of dihydrocleavamine.…”

Section: C) Cleavaminesmentioning

confidence: 99%

Progress in the Synthesis of Iboga-alkaloids and their Congeners

Jana

Paul

Sinha

2011

Organic Preparations and Procedures International

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“…As none of the many representatives containing a hydroxyl group at C (19), like compound 172, has been synthesized up to the present, we devised the retrosynthetic plan displayed in Scheme 30 [102] (for a short report, see [98]). The nature of R 3 in B is of little concern, since the two series are readily interconvertible at the indole alkaloid level [103]. The isoxazolidine precursor 174 should be constructed via an intramolecular nitrone-olefin [2+3]cycloaddition reaction of precursor 175, derived through oxidation from the piperidine derivative 176.…”

Section: Iboga Alkaloidsmentioning

confidence: 99%

New Strategies for the Synthesis of Monoterpene Indole Alkaloids

Borschberg

2005

COC

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The synthetic efforts of the author's research team in several areas within the monoterpene indole alkaloid family are summarized. Most of the work was accomplished in the field of the Aristotelia alkaloids, where some 25 natural products were synthesized for the first time. Systematic investigations on the oxidative rearrangement of indoles to oxindoles and pseudoindoxyl derivatives led to control over the chemoselectivity and stereoselectivity of this process, which served for enantioselective preparations of the simple alkaloids horsfiline and elacomine. In addition, recent developments in a novel approach to Iboga alkaloids containing a hydroxyl group at C(19) are presented. The key steps involved a self-immolating 1,4-chirality transfer in an Ireland-Claisen rearrangement and an intramolecular nitrone-olefin [2+3]-cycloaddition to give the aliphatic isoquinuclidine core of the target molecules. The first synthesis of (19R)hydroxyibogamine was completed by grafting a 3-ethylindole unit onto the aliphatic nitrogen, followed by closing the 7membered ring.

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Syntheses of velbanamine and catharanthine

Cited by 67 publications

References 1 publication

Formal Synthesis of (+)‐Catharanthine

Formal Synthesis of (+)‐Catharanthine

Progress in the Synthesis of Iboga-alkaloids and their Congeners

New Strategies for the Synthesis of Monoterpene Indole Alkaloids

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