Medium ring ethers by ring expansion-ring contraction: synthesis of lauthisan.
[reaction: see text] A new general method for the construction of medium ring ethers has been developed. This involves the ring expansion of halo-O,S-acetals followed by a Ramburg-Bäcklund ring contraction reaction with concomitant extrusion of the sulfur atom. This methodology has been utilized for the synthesis of cis- and trans-lauthisan.
Coster
Mark J
MJ
Department of Chemistry, University of Queensland, Brisbane 4072, Australia.
De Voss
James J
JJ
D000438:Alcohols / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D035964:Oxocins / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry
D000438:Alcohols; D001685:Biological Factors; D004988:Ethers, Cyclic; D007659:Ketones; D035964:Oxocins; D013440:Sulfides; C471499:lauthisan