title: Deslongchamps annulations with benzoquinone monoketals.
abstract: The so-called Deslongchamps annulation of deprotonated γ,δ-unsaturated β-ketoesters 15 to 2-(alkoxycarbonyl)cyclohex-2-en-1-ones or similarly activated cyclohex-2-en-1-ones offers a versatile access to various kinds of decalindiones. The scope of Deslongchamps annulations was extended by establishing acceptor-substituted benzoquinone monoketals such as 13 as viable substrates. They gave octalindiones such as 35 with diastereoselectivities ≥ 95:5.
authors.affiliation: Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Albertstr. 21, 79104 Freiburg im Breisgau, Germany.
authors.forename: Denis
authors.initials: D
authors.lastname: Petrović
authors.forename: Reinhard
authors.initials: R
authors.lastname: Brückner
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D007659:Ketones; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013148:Spironolactone / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D016227:Benzoquinones; D003512:Cyclohexanones; D007659:Ketones; D013141:Spiro Compounds; D013148:Spironolactone; C004532:quinone