Synthetic studies on taxanes: A domino-enyne metathesis/Diels-Alder approach to the AB-ring

Abstract

A domino enyne cross-metathesis/intramolecular Diels-Alder reaction has been successfully used to synthesize a bicyclo[5.3.1] undecene, corresponding to AB-ring of taxol without the gem dimethyl group.

Synthesis of Marine-Derived Carbasugar Pericosines

“…Hemiacetal 117 was first reduced with NaBH 4 , followed by CdC bond cleavage of vicinal diol 158 with NaIO 4 to afford hemiacetal 159 [123,124]. Subsequent nucleophilic addition of a vinyl Grignard reagent to 159 from the opposite side of the acetonide bridge, as shown by the dashed line, gave the antipode of 149 (ent-149), which could be transformed into (À)-2 and 3 in the same manner as described above.…”

A new and informative [a,b,c,d] nomenclature for one-pot multistep transformations: a simple tool to measure synthetic efficiency

“…In relation to our interest in the synthesis of taxol and its related structures, 17,18 we also developed the design and synthesis of hybrid natural products related to taxol. Hybrid molecules are functional adducts generated from two or more natural or unnatural molecules, each retaining their own structural features.…”