title: A general strategy for the stereocontrolled preparation of diverse 8- and 9-membered Laurencia-type bromoethers.
abstract: A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.
authors.affiliation: Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, United States. sas2197@columbia.edu
authors.forename: Scott A
authors.initials: SA
authors.lastname: Snyder
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Treitler
authors.forename: Alexandria P
authors.initials: AP
authors.lastname: Brucks
authors.forename: Wesley
authors.initials: W
authors.lastname: Sattler
mesh_terms: D054378:Acetogenins / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D044722:Laurencia / Q000737:chemistry*
chemical_list: D054378:Acetogenins; D004987:Ethers; D005663:Furans; D006842:Hydrocarbons, Brominated