2014
DOI: 10.1002/chem.201404295
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Formal Total Synthesis of (−)‐Taxol through Pd‐Catalyzed Eight‐Membered Carbocyclic Ring Formation

Abstract: A formal total synthesis of (-)-taxol by a convergent approach utilizing Pd-catalyzed intramolecular alkenylation is described. Formation of the eight-membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd-catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high efficiency of the Pd-catalyzed intramolecular alkenylation. Rearrangement of the epoxy benzyl ether through a 1,5… Show more

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Cited by 69 publications
(52 citation statements)
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“…The synthetic utility of this methodology was demonstrated by a four-step one-pot synthesis and a successful recycling of the reaction medium [127]. B-alkyl SMC, in particular, was likewise applied in the synthesis of beneficial products [130][131][132]. Two examples are shown in Scheme 16: Cytochalasin Z 8 and Ieodomycin D, which belong to the family of secondary fungal metabolite with a wide range of biological activities that target cytoskeletal processes [133][134][135].…”
Section: B-alkyl Smcs Using Bbn Variants (9-meo-9-bbn and Obbd Derivamentioning
confidence: 99%
See 1 more Smart Citation
“…The synthetic utility of this methodology was demonstrated by a four-step one-pot synthesis and a successful recycling of the reaction medium [127]. B-alkyl SMC, in particular, was likewise applied in the synthesis of beneficial products [130][131][132]. Two examples are shown in Scheme 16: Cytochalasin Z 8 and Ieodomycin D, which belong to the family of secondary fungal metabolite with a wide range of biological activities that target cytoskeletal processes [133][134][135].…”
Section: B-alkyl Smcs Using Bbn Variants (9-meo-9-bbn and Obbd Derivamentioning
confidence: 99%
“…B-alkyl SMC, in particular, was likewise applied in the synthesis of beneficial products [130][131][132]. Two examples are shown in Scheme 16: Cytochalasin Z8 and Ieodomycin D, which belong to the family of secondary fungal metabolite with a wide range of biological activities that target…”
Section: Selected Examples Of Applications Of Smcs and B-alkyl Smc Inmentioning
confidence: 99%
“…Palladium Catalyzed Alkenylation of a Methyl Ketone 13 We applied the palladium catalyzed alkenylation of a methyl ketone to the total synthesis of taxol. Two fragments, the A ring fragment 14 I and the C ring fragment 66, were assembled to afford 67 I as a single isomer via a halogen lithium exchange reaction (Scheme 21).…”
Section: Formal Total Synthesis Of ( ) Taxol Viamentioning
confidence: 99%
“…The spectacular clinical success of taxanes combined with their stunning complexity has motivated and inspired scores of chemists over the past several decades. [1][2][3] Indeed, Taxol (1, Figure 1) can be treated as ab arometer to measure progress and advances in the science of chemical synthesis.This iconic natural product has been prepared on ten separate occasions (seven total syntheses [4][5][6][7][8][9][10][11][12] and three formal syntheses [13][14][15][16] ), thus elegantly demonstrating the feasibility of its reconstitution by purely chemical means.Notwithstanding the beauty of these landmark accomplishments,t hey are eight to nine orders of magnitude less efficient than biological production. To be sure,m ere milligrams were produced all together by total synthesis,w hereas metric tons of Taxol are accessed every year through ap lant cell culture process developed by Bristol-Myers Squibb and Phyton Biotech, Inc.…”
mentioning
confidence: 99%