A stereo controlled route to a key intermediate fro the synthesis of maytansine

Samson, M.; Clercq, Pierre De; Wilde, H. De; Vandewalle, M.

doi:10.1016/s0040-4039(01)83195-6

Cited by 14 publications

(4 citation statements)

References 16 publications

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“…Through selective reduction of the γlactone derivative (341) and protection of compound 342 to form an intermediate (343) (mainly composed of formula E), the diol compound formed (344) was protected, and a Curtius re-arrangement of the azide gave the cyclic carbamate (345) (Figure 18). Samson et al [102] used (S)-(+)-4-hydroxy-2-cyclopentenone, which was readily available from the reaction with (R,R)-(+)-tartaric acid, as the starting material in the synthesis which was converted via the intermediates (346, 347 and 348) to the aldehydes (349 and 350) with the same configuration as C6 and C7, respectively. When the aldehyde group in compound 349 was treated with trimethylorthothioborate, compound 351a was produced.…”

Section: Chemical Synthesis Of Maytansine and Maytansine Fragmentsmentioning

confidence: 99%

“…Both compounds, 351a and 351b, can be regarded as potential acylanion equivalents (Figure 19). Samson et al [102] used (S)-(+)-4-hydroxy-2-cyclopentenone, which was readily available from the reaction with (R,R)-(+)-tartaric acid, as the starting material in the synthesis which was converted via the intermediates (346, 347 and 348) to the aldehydes (349 and 350) with the same configuration as C6 and C7, respectively. When the aldehyde group in compound 349 was treated with trimethylorthothioborate, compound 351a was produced.…”

Section: Chemical Synthesis Of Maytansine and Maytansine Fragmentsmentioning

confidence: 99%

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A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

Huang

Chen

et al. 2021

Molecules

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The genus Maytenus is a member of the Celastraceae family, of which several species have long been used in traditional medicine. Between 1976 and 2021, nearly 270 new compounds have been isolated and elucidated from the genus Maytenus. Among these, maytansine and its homologues are extremely rare in nature. Owing to its unique skeleton and remarkable bioactivities, maytansine has attracted many synthetic endeavors in order to construct its core structure. In this paper, the current status of the past 45 years of research on Maytenus, with respect to its chemical and biological activities are discussed. The chemical research includes its structural classification into triterpenoids, sesquiterpenes and alkaloids, along with several chemical synthesis methods of maytansine or maytansine fragments. The biological activity research includes activities, such as anti-tumor, anti-bacterial and anti-inflammatory activities, as well as HIV inhibition, which can provide a theoretical basis for the better development and utilization of the Maytenus.

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Section: Chemical Synthesis Of Maytansine and Maytansine Fragmentsmentioning

confidence: 99%

Section: Chemical Synthesis Of Maytansine and Maytansine Fragmentsmentioning

confidence: 99%

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

Huang

Chen

et al. 2021

Molecules

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“…To date they have accumulated five: Meyers [38] (1980), Corey [39] (1980), Isobe [40] (1982), Gao [41] (1988) and Huu [42] (1996). Additionally, the syntheses of fragments were published by Go ¨tschi [43], Ganem [44], Vandewalle [45], Barton [46], Ho [47], Fried [48] and Parsons [49]. Furthermore, the Confalone group reported studies on a new methodology for the ring closure using a nitrile oxideeolefine [3 þ 2] cycloaddition [50].…”

Section: Total Synthesis Of the Maytansinoidsmentioning

confidence: 99%

“…Thus, the aromatic moiety was prepared by Go ¨tschi [43], Meyers [38], Ganem [44], Corey [39] and Ho [47]. Ganem [44], Ho [47], Fried [48] and Parsons [49] dealt with the construction of the carbamoyl system in the eastern fragment and Vandewalle [45] and Barton [46] directed their efforts mainly on the installation of the correct stereochemistry at C6 and C7 (Fig. 7).…”

Section: Retrosynthetic Analyses Of the Total Syntheses And Fragmentsmentioning

confidence: 99%

The chemistry and biology of the maytansinoid antitumor agents

Kirschning

Harmrolfs

Knobloch

2008

Comptes Rendus. Chimie

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Maytansine (1) and its congeners have been isolated from higher plants, mosses and from an Actinomycete, Actinosynnema pretiosum. The ansamitocins P-1 to P-4 (11be11e) are structurally closely related macrolactam antibiotics which have been obtained from bacterial sources, mainly A. pretiosum. Many of these compounds are antitumor agents of extraordinary potency. Detailed structureeactivity relationship (SAR) studies have been hampered by the accessibility of analogues in sufficient amounts. The present review focuses on several synthetic approaches towards the maytansinoids which include total synthesis, semisynthesis and mutational biosynthesis utilising genetically engineered microorganisms.

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Tris(ethylthio)borane

2001

Encyclopedia of Reagents for Organic Synthesis

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A stereo controlled route to a key intermediate fro the synthesis of maytansine

Cited by 14 publications

References 16 publications

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

The chemistry and biology of the maytansinoid antitumor agents

Tris(ethylthio)borane

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