Eine neue synthese von vinblastin-derivaten VI, synthese von 20'-desethyl-20'-desoxy-c'-homovinblastin

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

doi:10.1016/s0040-4020(01)86687-4

Cited by 7 publications

(9 citation statements)

References 9 publications

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“…334–339 The condensation between the amine and pentafluorophenyl esters was applied to the successful synthesis of three different ring systems of bridged lactams. 336–338 The presence of an additional substituent (cf. 195b ) 336 was found to be crucial in obtaining bridged products.…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On One-carbmentioning

confidence: 99%

“…In contrast, the cyclization of the indole-derived amino acids was less general, affording only a [4.4.1] ring system in modest yield (Scheme 50). 338 Magnus and coworkers reported the synthesis of a related bridged lactam 199 containing a [4.3.1] ring system as a part of their studies towards the synthesis of vinblastine (Scheme 51a). 340,341 The transannular cyclization between the methyl ester and amine proceeded smoothly under thermal conditions.…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On One-carbmentioning

confidence: 99%

“…337 Although these authors also accomplished a related α-arylation of [4.4.1] ring system, 339 the reaction of a bridged lactam with [4.3.1] scaffold was unsuccessful due to its instability to the reaction conditions. 336 …”

Section: Reactivity Of Bridged Lactams and Related Heterocyclesmentioning

confidence: 99%

“…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%

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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 N–(co) Bond On One-carbmentioning

confidence: 99%

Section: Synthesis Of Bridged Lactams With N–(co) Bond On One-carbmentioning

confidence: 99%

Section: Reactivity Of Bridged Lactams and Related Heterocyclesmentioning

confidence: 99%

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

confidence: 99%

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Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…Further chemistry was undertaken in order to improve the synthesis of such homo-vinblastine 30 [25], but its biological properties have not been described, and no further publications have appeared.…”

Section: Modifications Of the C' Ringmentioning

confidence: 99%

Modifications in the upper or Velbenamine Part of the Vinca Alkaloids have Major Implications for Tubulin Interacting Activities

Fahy

2001

CPD

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Vinca alkaloids represent a chemical class of major interest in cancer chemotherapy. The lead compounds vinblastine and vincristine have been employed in clinical practice for more than thirty years and remain widely used to this day. Several hundred derivatives have been synthesised and evaluated for their pharmacological activities, the majority being modified in the vindoline moiety, bearing several reactive centers. These efforts led to the identification of the amido derivative vindesine, registered in Europe in 1980 and now available in several countries. Then novel chemistry permitted the semisynthesis of derivatives modified in the velbenamine "upper" part of the molecule, creating a new potential in the Vinca alkaloids medicinal chemistry: as a result, vinorelbine, obtained by C' ring contraction of anhydrovinblastine, and is now marketed worldwide. Several strategies aimed at the total synthesis of vinblastine derivatives have been investigated, giving the opportunity to design rationally certain compounds. Modifications in the D' ring appeared to induce dramatic changes in the tubulin interactions. These observations have been confirmed recently by the identification of unprecedented pharmacological properties exerted by the novel fluorinated Vinca alkaloid, vinflunine. This review will focus more specifically on derivatives which have been modified in the velbenamine part, with the aim of inducing different chemical and pharmacological properties.

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ChemInform Abstract: Novel Synthesis of Vinblastine Derivatives. Part 6. Synthesis of 20′‐Deethyl‐20′‐deoxy‐C′‐homovinblastine.

et al. 1990

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308ChemInform Abstract The coupling of the azecinoindole derivative (I) with vindoline (II) via the respective chloroindolenine leads, after cyclization, to a mixture of the major isomers (IVa), (IVb) and the minor isomers (IVc), (IVd). The required title compound (IVa) can be isolated in a 27% yield. Reaction of the known homocleavamine derivative (V), however, leads to (IVc) + (IVd) as the main products. Some model studies designing the methodology used are performed before.

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Eine neue synthese von vinblastin-derivaten VI, synthese von 20'-desethyl-20'-desoxy-c'-homovinblastin

Cited by 7 publications

References 9 publications

Chemistry of Bridged Lactams and Related Heterocycles

Chemistry of Bridged Lactams and Related Heterocycles

Modifications in the upper or Velbenamine Part of the Vinca Alkaloids have Major Implications for Tubulin Interacting Activities

ChemInform Abstract: Novel Synthesis of Vinblastine Derivatives. Part 6. Synthesis of 20′‐Deethyl‐20′‐deoxy‐C′‐homovinblastine.

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