Total syntheses of naturally occurring diacetylenic spiroacetal enol ethers.
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.
Miyakoshi
Naoki
N
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Aburano
Daisuke
D
Mukai
Chisato
C
D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry
C503525:(2E)-methoxymethylidene-1,6-dioxaspiro(4.5)decane; D000475:Alkenes; D004852:Epoxy Compounds; D013141:Spiro Compounds; D013644:Tartrates; C478877:diacetylenic spiroacetal enol ether epoxide; D010165:Palladium; C064501:diethyl tartrate