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- W4211256003 endingPage "6343" @default.
- W4211256003 startingPage "6339" @default.
- W4211256003 abstract "Countless natural products of polyketide origin have an E-configured 2-methyl-but-2-en-1-ol substructure. An unconventional entry into this important motif was developed as part of a concise total synthesis of 5,6-dihydrocineromycin B. The choice of this particular target was inspired by a recent study, which suggested that the cineromycin family of antibiotics might have overlooked lead qualities, although our biodata do not necessarily support this view. The new approach consists of a sequence of alkyne metathesis followed by a hydroxy-directed trans-hydrostannation and a largely unprecedented methyl-Stille coupling. The excellent yield and remarkable selectivity with which the signature trisubstituted alkene site of the target was procured is noteworthy considering the rather poor outcome of a classical ring-closing metathesis reaction. Moreover, the unorthodox ruthenium-catalyzed trans-hydrostannation is shown to be a versatile handle for diversity-oriented synthesis." @default.
- W4211256003 created "2022-02-13" @default.
- W4211256003 creator A5012719319 @default.
- W4211256003 creator A5019345265 @default.
- W4211256003 creator A5054667122 @default.
- W4211256003 creator A5068877238 @default.
- W4211256003 date "2015-04-13" @default.
- W4211256003 modified "2023-10-17" @default.
- W4211256003 title "Selective Formation of a Trisubstituted Alkene Motif by<i>trans</i>-Hydrostannation/Stille Coupling: Application to the Total Synthesis and Late-Stage Modification of 5,6-Dihydrocineromycin B" @default.
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