Eine neue synthese von vinblastin-derivaten II

Schill, Gottfried; Löwer, Hartmut; Priester, C. U.; Windhövel, Udo Frank; Fritz, Hans

doi:10.1016/s0040-4020(01)86861-7

Cited by 17 publications

(4 citation statements)

References 58 publications

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“…In 1987, using a transannular cyclization under thermal conditions, Schill developed the synthesis of indole-derived bridged lactams 195 as potential precursors to higher analogues of vinca alkaloids (Scheme ). − The condensation between the amine and pentafluorophenyl esters was applied to the successful synthesis of three different ring systems of bridged lactams. − The presence of an additional substituent (cf. 195b ) was found to be crucial in obtaining bridged products.…”

Section: Synthesis Of Bridged Lactams With the N–(co) Bond On A One-c...mentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Synthesis Of Bridged Lactams With the N–(co) Bond On A One-c...mentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…Another model study, using harmicine as the starting point, was published in 1987 by Schill and coworkers [41][42][43]. The study was aimed at the synthesis of vinblastine beginning with one-half of this bisindole alkaloid molecule.…”

Section: Methodsmentioning

confidence: 99%

Harmicine, a Tetracyclic Tetrahydro-β-Carboline: From the First Synthetic Precedent to Isolation from Natural Sources to Target-Oriented Synthesis (Review)*

Lood

Koskinen

2014

Chem Heterocycl Comp

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“…The C(3)- N b bond cleavage [114,115,116,117,118,119,120,121] was carried out analogous to the procedure reported by Bonjoch et al [114]. Pericyclivine 92 when heated to reflux in methanol, and reacted with benzyl chloroformate, to furnish the carbamate 94 in 75% yield (Scheme 9).…”

Section: Partial and Total Synthesis Of Bisindole Alkaloidsmentioning

confidence: 99%

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

2016

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Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthesis of bisindole alkaloids isolated primarily from the Alstonia genus of the Apocynaceae family. The monomeric units belong to the sarpagine, ajmaline, macroline, vobasine, and pleiocarpamine series. An up-to-date discussion of their isolation, characterization, biological activity as well as approaches to their partial and total synthesis by means of both synthetic and biosynthetic strategies are presented.

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Eine neue synthese von vinblastin-derivaten II

Cited by 17 publications

References 58 publications

Chemistry of Bridged Lactams and Related Heterocycles

Chemistry of Bridged Lactams and Related Heterocycles

Harmicine, a Tetracyclic Tetrahydro-β-Carboline: From the First Synthetic Precedent to Isolation from Natural Sources to Target-Oriented Synthesis (Review)*

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

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