“…Recently, d'Angelo has demonstrated the efficacy of a titanium(IV)-mediated Michael-type intramolecular ring closure in silyl enol ether 276 to a tricyclic ring C aromatic taxoid 277 , Scheme . 54 …”
“…The intermediate 275, in particular, has been employed for a successful synthesis of the diterpene natural product taxusin. 116 Recently, d'Angelo has demonstrated 117 the efficacy of a titanium(IV)-mediated Michael-type intramolecular ring closure in silyl enol ether 276 to a tricyclic ring C aromatic taxoid 277, Scheme 54.…”
“…Recently, d'Angelo has demonstrated the efficacy of a titanium(IV)-mediated Michael-type intramolecular ring closure in silyl enol ether 276 to a tricyclic ring C aromatic taxoid 277 , Scheme . 54 …”
“…The intermediate 275, in particular, has been employed for a successful synthesis of the diterpene natural product taxusin. 116 Recently, d'Angelo has demonstrated 117 the efficacy of a titanium(IV)-mediated Michael-type intramolecular ring closure in silyl enol ether 276 to a tricyclic ring C aromatic taxoid 277, Scheme 54.…”
“…In 1998, d'Angelo and co-workers 119 reported a Mukaiyama−Michael reaction approach to the taxane skeleton (Scheme 21B). Thus, treatment of silyl enol ether 150a in the presence of TiCl 4 resulted in a Mukaiyama−Michael reaction to afford the ABC taxoid core 150b as a 2:1 mixture of diastereomers in 61% yield.…”
Taxol (paclitaxel), the most well-known taxane diterpenoid, is the best-selling natural-source anticancer drug ever produced and one of the most common prescriptions in the treatment of breast, lung, and ovarian cancers, saving countless lives around the world. Structurally, Taxol possesses a highly oxygenated [6−8−6−4] core bearing 11 stereocenters, seven of which are contiguous chiral centers. Moreover, the extremely strained bicyclo[5.3.1] undecane ring system with a bridgehead double bond is a unique structural feature. All these features make Taxol a highly challenging synthetic target. Tremendous synthetic efforts from more than 60 research groups around the world have already culminated in ten total syntheses and three formal syntheses, as well as more than 60 synthetic model studies of Taxol. This review is intended to provide a long-overdue appraisal of the great achievements in the total syntheses of Taxol reported in the last few decades. In doing so, we summarize the development of synthesis toward Taxol from 1994 to 2022, including the evolution of synthetic strategy for accessing this complex molecular scaffold and key lessons learned from such endeavors. Finally, we briefly discuss the future of the research in this area.
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