70863-78-4Relevant academic research and scientific papers
Total synthesis of (±)-hibiscone C
Ungureanu, Sinziana,Meadows, Maggie,Smith, Joel,Duff, David B.,Burgess, James M.,Goess, Brian C.
scheme or table, p. 1509 - 1511 (2011/06/10)
A total synthesis of (±)-hibiscone C, one member of the furanosteroid family of natural products that also includes viridin and wortmannin, is reported. Two new pathways for formation of the key diacyl furan subunit are described.
Intramolecular Photocyclizations. 2. Total Synthesis of (+/-)-Hibiscone C (Gmelofuran)
Koft, Emil R.,Smith, Amos B.
, p. 2115 - 2121 (2007/10/02)
We describe here a full account of the first total synthesis of (+/-)-hibiscone C (gmelofuran) (1), a structurally novel furanosesquiterpene isolated from the heartwood of Hibiscus elatus (Blue Mahoe), the national tree of Jamaica.The synthesis proceeds i
Naturally Occurring Quinones. Part 27. Sesquiterpenoid Quinones and Related Compounds from Hibiscus elatus: Crystal Structure of Hibiscone C (Gmelofuran)
Ferreira, Margarida A.,King, Trevor J.,Ali, Sadaquat,Thomson, Ronald H.
, p. 249 - 256 (2007/10/02)
The blue-grey or pink-grey heartwood of Hibiscus elatus (Blue Mahoe), which turns to light yellow or buff-grey on exposure to light, contains a group of colourless sesquiterpenoid ketones (hibiscones A - D) and o-naphthoquinones (hibiscoquinones A - D) based on a cadinane skeleton.The structure of the furanodiketone, hibiscone C (gmelofuran) (3) was determined by X-ray crystallography, to which hibiscones A, B, and C were related by spectroscopic and chemical methods.Hibisquinones B and C fade slowly in light but hibisquinone A, 8-formyl-7-hydroxy-5-isopropyl-3-methyl-1,2-naphthoquinone, is very photolabile and rearranges quickly in daylight to a colourless lactone.The model compound 8-formyl-7-hydroxy-1,2-naphthoquinone behaves in the same way while 8-formyl-7-hydroxy-1,4-naphthoquinone rearranges much more slowly in daylight to an isomeric lactone.
