Synthesis of the putative structure of tridachiahydropyrone.
[reaction: see text] A short total synthesis of the putative structure of the marine natural product tridachiahydropyrone as a single enantiomer is described. Novel steps include a cuprate addition and cyclization to form a cyclohexanone ring and formation of the bicyclic pyrone with P(2)O(5) on Celite. The spectroscopic data obtained for compound 1 do not match those reported for tridachiahydropyrone; therefore, revision of the assigned natural product structure is warranted.
Jeffery
David W
DW
School of Chemistry, Physics and Earth Sciences, Flinders University, G.P.O. Box 2100, Adelaide, S.A. 5001, Australia.
Perkins
Michael V
MV
White
Jonathan M
JM
D000818:Animals; D003500:Cyclization; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D011753:Pyrones; C507269:tridachiahydropyrone