Cyanolide A was isolated from the extracts of cyanobacteria; Lyngbya bouillonii, that was found off the shallow reef wall in Papua New Guinea.1 Cyanolide A exhibits molluscicidal properties against the snail vector Biomphalaria glabrata that can be useful in the control of schistosomiasis. In our synthesis of Cyanolide A, the Oxa-Michael cyclisation was utilized to form the tetrahydropyran core ring. The synthesis of Cyanolide A to form the tetrahydropyran precursor was done by integrating the xylose derivative into the synthesis scheme in the beginning to avoid the use of protecting group. This is done by the glycosylation of 4 with the xylose derivative to obtain the β-xylose derivative. Cyanolide A can be achieved via a tandem deprotection Oxa-Michael cyclisation of compound 4. Selected References: 1. Alban R. Pereira, Christine F. McCue, and Wiliam H. Gerwick. J. Nat. prod. 2010, 73, 217 2. Roderick W. Bates, Tee Guan Lek, Synthesis, 2014, 46, 1731

Total synthesis of cyanolide A

249th National Meeting (2015)

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