title: Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.
abstract: Herein we describe a scalable approach to the decalin moiety of maklamicin. Key to the synthesis is an intramolecular Diels-Alder (IMDA) reaction that proceeds via anendo-axial transition state to generate the desired stereochemistry. We explored the diastereoselectivity of the IMDA reaction as a function of both chiral catalysis and acyclic precursor stereochemistry.
authors.affiliation: Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA.
authors.forename: Michelle H
authors.initials: MH
authors.lastname: Lacoske
authors.affiliation: Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA. ; Department of Chemistry, South University of Science and Technology of China, Shenzhen, Guangdong 518055, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Xu
authors.affiliation: Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA.
authors.forename: Noel
authors.initials: N
authors.lastname: Mansour
authors.affiliation: Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA.
authors.forename: Chao
authors.initials: C
authors.lastname: Gao
authors.affiliation: Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA.
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis