Journal
ORGANIC LETTERS
Volume 10, Issue 23, Pages 5477-5480Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802297h
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Funding
- Engineering and Physical Sciences Research Council [EP/E048463/1]
- EPSRC [EP/E048463/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/E048463/1] Funding Source: researchfish
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The core structure of the RNA polymerase inhibitor tagetitoxin has been synthesized by one-carbon ring expansion of bridged bicyclic monothioacetals. The key steps are intramolecular ylide formation by reaction between the sulfur atom and a pendant diazoester, followed by an efficient photochemical 1,2-rearrangement to give the desired 9-oxa-3-thiabicyclo[3.3.1]nonane ring system.
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