74740-97-9Relevant academic research and scientific papers
Marine Terpenes and Terpenoids. 12. Autoxidation of Dihydrofuranocembranoids
Kobayashi, Masaru
, p. 2840 - 2852 (2007/10/02)
Dihydrofuranocembranoids 16-deoxosarcophine (1), sarcophytonin A (3) and sarcophytonin C (5), isolated from Sarcophyton sp. soft coral, afforded the butenolides sarcophine (2), sarcophytonin B (4) and sarcophytonin D (6), respectively, during storage. 16-Deoxosarcophine (1) when subjected to autoxidation in CHCl3 at room temperature for ten days afforded 2 and epimers of hydroperoxy-γ-ylidenebutenolides (8a and 8b) as major products, and a furan (7) and epimers of hydroxy-γ-ylidenebutenolides (9a and 9b) as minor products.The furan 7 decomposed further giving the butenolides 8a,b and 9a,b.The autoxidation process was interpreted as being initiated by the formation of the C-16 hydroperoxide 11 which gives the butenolide 2, and the furan 7 which subsequently reacts with singlet oxygen leading to the γ-ylidenebutenolides 8a, 8b, 9a and 9b.
