Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B.
[reaction: see text] The total syntheses of racemic sesterpenic acids 1 and 2 have been accomplished from creosol (6) in 12 and 13 steps, respectively. Intramolecular Diels-Alder reaction of masked o-benzoquinone 7 generated from 6 and allyl alcohol, stereoselective addition of alkenylcerium(III) chloride 8 to ketone 5, and anionic oxy-Cope rearrangement of dienol 4 are the key steps.
Hsu
Day-Shin
DS
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.
Liao
Chun-Chen
CC
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D011161:Porifera; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D009281:Naphthalenes; D013729:Terpenes; C410133:bilosespen A; C410134:bilosespen B; C007229:decalin