Total Synthesis of Thailanstatin A.
The total synthesis of the spliceosome inhibitor thailanstatin A has been achieved in a longest linear sequence of nine steps from readily available starting materials. A key feature of the developed synthetic strategy is the implementation of a unique, biomimetic asymmetric intramolecular oxa-Michael reaction/hydrogenation sequence that allows diastereodivergent access to highly functionalized tetrahydropyrans, which can be used for the synthesis of designed analogues of this bioactive molecule.
Department of Chemistry, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
K C
KC
Nicolaou
Derek
D
Rhoades
Manjunath
M
Lamani
Manas R
MR
Pattanayak
S Mothish
SM
Kumar
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D055808:Drug Discovery; D006865:Hydrogenation; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017381:Spliceosomes / Q000187:drug effects
D000970:Antineoplastic Agents; D011714:Pyrans; C582010:thailanstatin A