Total Syntheses of Naturally Occurring Diacetylenic Spiroacetal Enol Ethers
journal contributionposted on 22.07.2005 by Naoki Miyakoshi, Daisuke Aburano, Chisato Mukai
Any type of content formally published in an academic journal, usually following a peer-review process.
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.