The first total synthesis of lajollamycin B, as tructurally novel nitro-tetraene spiro-b-lactone/g-lactonea ntibiotic, is described. The convergent synthesis involves the construction of the C8'-C11' nitrodienylstannane and its coupling with the segment prepared from the C1'-C7' w-iodo-heptadienoic acid and the right-hand heterocyclic fragment, which has been utilized for our previouss yntheses of oxazo-lomycinA.T he revisiono ft he geometry of the terminal D 10',11' -double bond from E to Z is also described for the structure of natural lajollamycin B.
The total synthesis of (-)-englerin A, a potent and selective inhibitor of renal cancer cell lines, is described. The key feature includes the stereocontrolled construction of the cyclopentane structure by taking advantage of a base-promoted epoxynitrile cyclization.
The highly stereocontrolled total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate is described, which features the expeditious construction of a bicyclo[4.3.1]decane ring system by a palladium-catalyzed tandem enolate allylation/arylation reaction.
A formal
synthesis of (−)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of
the synthesis includes the highly stereoselective tandem radical reaction
to construct the azabicyclo[3.3.1]nonane core and the enantioselective
formation of an all-carbon quaternary center via the Pd-mediated deracemization.
The first total synthesis of thuggacin cmc-A and the determination of the absolute structure are described. The thuggacin family of antibiotics is of great interest due to the antibiotic activity against Mycobacterium tuberculosis. Based on the assumption that seven stereogenic centers in thuggacin cmc-A would share the same stereochemistry as thuggacin-A, all stereogenic centers of thuggacin cmc-A were strictly constructed in a stereocontrolled manner. The total synthesis allowed its stereostructure to be fully confirmed.
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