Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 12, Pages 8019-8026Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00870
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Funding
- Japan Society for the Promotion of Science (JSPS) [17K05779]
- Smithsonian Tropical Research Institute's Research Opportunity Fund
- Grants-in-Aid for Scientific Research [17K05779] Funding Source: KAKEN
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A new strategy for the synthesis of 23-, 25-, 27-, and 29-membered (Z)-selective unsaturated and saturated macrocyclic lactones from commercially available 16- and 17-membered macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi macrolactonization, and photoinduced decarboxylative radical macrolactonization is described. The position of the unsaturated part in the macrocyclic lactones can be controlled by changing the number of carbons in the starting materials. This protocol can provide facile access to the desired large-ring (Z)-selective unsaturated and saturated macrocyclic lactones from simple starting materials.
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