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-hydride shift, generating the C3 stereogenic center and subsequently forming the C1-C2 benzylidene, was discovered and utilized in the preparation of a substrate for the Pd-catalyzed reaction.
Original language | English |
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Pages (from-to) | 355-359 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 21 |
Issue number | 1 |
DOIs | |
Publication status | Published - 2015 Jan 2 |
Keywords
- Cyclization
- Enantioselectivity
- Natural products
- Palladium
- Total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry