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Title

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

AuthorsLi, Song-Wei; Mudianta, I. Wayan; Cuadrado, Cristina; Geng, Li; Yudasmara, Gede A.; Setiabudi, Gede I. ; Hernández Daranas, Antonio CSIC ORCID ; Guo, Yue-Wei
KeywordsCarbon
Chemical structure
Molecular structure
Nuclear magnetic resonance spectroscopy
Mathematical methods
Issue Date3-Sep-2021
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 86(17): 11771–11781 (2021)
AbstractLitosetoenins 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.
Publisher version (URL)https://doi.org/10.1021/acs.joc.1c01218
URIhttp://hdl.handle.net/10261/249688
DOIhttp://dx.doi.org/10.1021/acs.joc.1c01218
ISSN0022-3263
E-ISSN1520-6904
Appears in Collections:(IPNA) Artículos
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