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Total Syntheses of Naturally Occurring Diacetylenic Spiroacetal Enol Ethers

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journal contribution
posted on 22.07.2005 by Naoki Miyakoshi, Daisuke Aburano, Chisato Mukai
A highly stereoselective method for constructing a (2E)-methoxymethylidene-1,6-dioxaspiro[4.5]decane skeleton has been developed on the basis of the palladium(II)-catalyzed ring-closing reaction of the 3,4-dioxygenated-9-hydroxy-1-nonyn-5-one derivatives as a crucial step. The newly developed procedures could be successfully applied to the first total synthesis of five diacetylenic spiroacetal enol ether natural products starting from commercially available (R,R)- or (S,S)-diethyl tartrate.