Natural Taxanes: Developments Since 1828

Wang, Yu Fang; Shi, Qing; Dong, Ming; Kiyota, Hiromasa; Gu, Yu‐Cheng; Cong, Bin

doi:10.1021/cr100147u

Cited by 183 publications

(155 citation statements)

References 457 publications

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“…3 In addition to its potent bioactivity, taxol features a highly distorted 6 8 6 tricyclic bridged scaffold bearing nine stereogenic centers, including an all carbon quaternary stereogenic center, a variety of functional groups (such as oxetane, trans 1,2 diol, acyloin, and a bridgehead double bond), and an amino alcohol side chain linked by an ester.…”

Section: Introductionmentioning

confidence: 99%

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Formal Total Synthesis of (−)-Taxol

Utsugi¹,

Iwamoto²,

Hirai³

et al. 2017

J. Synth. Org. Chem. Jpn.

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Formal total synthesis of ( ) taxol is described herein. This convergent synthesis was accomplished by utilizing two chiral fragments, both of which were prepared via asymmetric catalysis. A palladium catalyzed reaction was found to afford the eight membered ring effectively, i.e., a B alkyl Suzuki Miyaura coupling reaction and an intramolecular alkenylation of a methyl ketone successfully constructed the B ring of taxol in excellent yield. During the preparation of a substrate for the palladium catalyzed reaction, a unique rearrangement of the epoxy benzyl ether, via a 1,5 hydride shift that generates the C3 stereogenic center and subsequently forms the C1 C2 benzylidene moiety, was observed. Strenuous efforts were required for transformations after the construction of the taxane scaffold to achieve the formal total synthesis of taxol because very few approaches are available for the synthesis of the target compound.

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Section: Introductionmentioning

confidence: 99%

“…Indeed, the epoxidation of 49 with VO(acac) 2 and TBHP 44 afforded epoxide 52 as the single isomer (Scheme 15). The yield was improved to 94% by the use of less acidic VO(OEt) 3 . 45 The stereoselectivity is well explained by allylic hydroxy group directed epoxidation, as depicted in Scheme 15.…”

mentioning

confidence: 99%

Formal Total Synthesis of (−)-Taxol

Utsugi¹,

Iwamoto²,

Hirai³

et al. 2017

J. Synth. Org. Chem. Jpn.

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“…1) [2,3]. Cephalomannine also has important bioactivity [4]. Moreover, 10-DAB and baccatin III can be transferred to paclitaxel or its derivatives through the biosynthesis or chemosynthesis methods [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of molecular imprinted polymer functionalized with core/shell magnetic particles (Fe 3 O 4 @SiO 2 @MIP) for the simultaneous recognition and enrichment of four taxoids in Taxus × media

Fan

et al. 2015

Chemical Engineering Journal

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“…So far more than 550 taxanes have been identified, and new taxanes continue to be isolated from the needles, bark, stem, and roots of Taxus species. 1 Although taxol and its derivatives are widely used in clinical applications, the chemotherapy often fails due to its acquired-drug resistance, neuro-cytotoxicity, and low oral bioavailability. Thus, there is continuously demanding of new information facilitating the novel taxane-based drug design and discovery.…”

mentioning

confidence: 99%