title: Progress toward the total synthesis of (±)-havellockate.
abstract: Havellockate (1) was isolated from the soft coral Sinularia granosa located on the Havellock island in the Indian Ocean. This highly compact and polyoxygenated marine diterpene bears a cis-fused hydrindane core that contains eight stereogenic centers as well as a spiro-lactone. To the best of our knowledge, no syntheses of 1 have been reported yet. Herein, we describe the synthesis of the all-carbon framework of havellockate (1) in 18 chemical operations. Our approach highlights the efficiency and utility of the hydroxy-directed Diels-Alder (HDDA) reaction to quickly access the cis-fused hydrindane core and securing the correct stereochemistry at C6 and C7. Moreover, six of the eight stereogenic centers have been installed in the correct stereochemistry.
authors.affiliation: Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Canada K1N 6N5.
authors.forename: Rachel L
authors.initials: RL
authors.lastname: Beingessner
authors.forename: Julie A
authors.initials: JA
authors.lastname: Farand
authors.forename: Louis
authors.initials: L
authors.lastname: Barriault
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C554583:havellockate