title: Strategies for the Total Synthesis of Diverse Bromo-Chamigrenes.
abstract: Several dozen spirocyclic sesquiterpenoids known as the bromo-chamigrenes have been isolated to date. Yet, despite their unique structures, synthetic efforts toward this collection have been modest. Herein, we outline two strategies to generate their skeletons based on (1) a biomimetic bromonium-induced polyene cyclization using BDSB (Et2SBr·SbCl5Br) and (2) a Diels-Alder reaction which ultimately delivered four members of the class. In addition, X-ray crystallography reveals that one member has a structure in need of revision.
authors.affiliation: Dept. of Chemistry, The University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.|Dept. of Chemistry, The Scripps Research Institute , 130 Scripps Way, Jupiter, Florida 33458, United States.
authors.forename: Minxing
authors.initials: M
authors.lastname: Shen
authors.affiliation: Dept. of Chemistry, Columbia University , 3000 Broadway, New York, New York 10027, United States.
authors.forename: Manuel
authors.initials: M
authors.lastname: Kretschmer
authors.affiliation: Dept. of Chemistry, Columbia University , 3000 Broadway, New York, New York 10027, United States.
authors.forename: Zachary G
authors.initials: ZG
authors.lastname: Brill
authors.affiliation: Dept. of Chemistry, The University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.|Dept. of Chemistry, The Scripps Research Institute , 130 Scripps Way, Jupiter, Florida 33458, United States.|Dept. of Chemistry, Columbia University , 3000 Broadway, New York, New York 10027, United States.
authors.forename: Scott A
authors.initials: SA
authors.lastname: Snyder