Litosetoenins A–E, Diterpenoids from the Soft Coral Litophyton setoensis, Backbone-Rearranged through Divergent Cyclization Achieved by Epoxide Reactivity Inversion

Litosetoenins A–E (1–5), five new ring-rearranged serrulatane-type diterpenoids with a common tricyclo[3.0.4]decane core, along with a known diterpenoid glycoside (6), a related known diterpenoid (7), and four known sesquiterpenoids (8–11), were isolated from a Balinese soft coral Litophyton setoensis. Spirolitosetoenin A (5a) and isospirolitosetoenin A (5b), featuring an unprecedented spiro[4,5]decane core, were obtained after treatment of compound 5 with HCl in methanol. The structures of new compounds were elucidated by extensive spectroscopic analysis, quantum mechanical nuclear magnetic resonance approach, and chemical methods. A plausible biosynthetic pathway involving an unusual divergent biogenesis was proposed.

Bibliographic Details

Main Authors:	Li, Song-Wei, Mudianta, I. Wayan, Cuadrado, Cristina, Geng, Li, Yudasmara, Gede A., Setiabudi, Gede I., Hernández Daranas, Antonio, Guo, Yue-Wei
Other Authors:	National Natural Science Foundation of China
Format:	artículo biblioteca
Language:	English
Published:	American Chemical Society 2021-09-03
Subjects:	Carbon, Chemical structure, Molecular structure, Nuclear magnetic resonance spectroscopy, Mathematical methods,
Online Access:	http://hdl.handle.net/10261/249688 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100001809
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