First asymmetric synthesis of the cyclohexanone subunit of baconipyrones A and B. Revision of its structure.
[reaction: see text] An asymmetric synthesis of the 3,5-dihydroxycyclohexanone subunit of baconipyrones A and B, as well as that of the hydroxydiketone subunit of baconipyrones C and D ((-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione), is described. Key steps include sulfur dioxide-induced additions of enoxysilanes to 1,3-dioxy-1,3-dienes, followed by retro-ene desulfitations (retro-ene elimination of SO(2)).
Laboratory of Glycochemistry and Asymmetric Synthesis, BCH, Swiss Federal Institute of Technology (EPFL), CH-1015 Lausanne, Switzerland.
Māris
M
Turks
M Carmen
MC
Murcia
Rosario
R
Scopelliti
Pierre
P
Vogel
D000818:Animals; D002384:Catalysis; D003500:Cyclization; D003510:Cyclohexanes / Q000737:chemistry; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013458:Sulfur Dioxide / Q000737:chemistry
D003510:Cyclohexanes; D011753:Pyrones; C430470:baconipyrone A; C430469:baconipyrone B; D013458:Sulfur Dioxide; C410203:baconipyrone C