期刊
ORGANIC LETTERS
卷 15, 期 8, 页码 1798-1801出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol400165x
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资金
- EPSRC [EP/G010250]
- Royal Society
- Engineering and Physical Sciences Research Council [EP/G010250/1] Funding Source: researchfish
- EPSRC [EP/G010250/1] Funding Source: UKRI
A concise and highly convergent three-step total synthesis of the lactarane natural product, pyrovellerolactone, is described. The key step involves a regio- and diastereoselective Modiunnatalyzed [(3 + 2) + 2] carbocyclization of an alkenylidenecyclopropane with a 4-hydroxybut-2-ynoate followed by an in situ intramolecular lactonization to generate the tricyclic core in a single operation. This represents the first example of a higher-order [3 + 2 + 2] carbocyclization reaction in total synthesis, which is likely to provide an important strategy for the construction of related targets within this sesquiterpene family.
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