期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 350, 期 4, 页码 557-560出版社
WILEY-BLACKWELL
DOI: 10.1002/adsc.200700537
关键词
antibiotics; asymmetric synthesis; metathesis; natural products; ruthenium; spiro compounds
Routiennocin is a member of a family of polycyclic pyrrole ether antibiotics that simultaneously uncouple oxidative phosphorylation and inhibit ATPase as a result of selective complexation of divalent metal ions. We describe a concise synthesis of routiennocin with the longest linear sequence of 8 steps. Our synthesis features a unique bi-directional strategy, which entails a sequential ring-opening/cross metathesis of a highly strained cyclopropenone acetal. This approach enables rapid and highly convergent assembly of the fully extended polyketide subunit of this natural product from readily available homoallylic alcohol precursors.
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