Progress toward the total synthesis of (±)-havellockate.
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.
Beingessner
Rachel L
RL
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Canada K1N 6N5.
Farand
Julie A
JA
Barriault
Louis
L
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D004224:Diterpenes; C554583:havellockate