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Biomimetic Synthesis of Macahydantoins A and B from Lepidium meyenii, and Structure Revision of Macahydantoin B as a Class of Thiohydantoin with a 4-Methyl-hexahydropyrrolo[1,2-c]imidazole Skeleton.
Zhou, Min; Ma, Hang-Ying; Xing, Huan-Huan; Li, Ping; Li, Gan-Peng; Geng, Hui-Chun; Hu, Qiu-Fen; Yang, Guang-Yu.
Afiliación
  • Zhou M; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, Yunnan People's Republic of China.
  • Ma HY; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, Yunnan People's Republic of China.
  • Xing HH; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, Yunnan People's Republic of China.
  • Li P; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, Yunnan People's Republic of China.
  • Li GP; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, Yunnan People's Republic of China.
  • Geng HC; Institute of Quality Standard and Testing Technology, Yunnan Academy of Agricultural Science , Kunming 650223, Yunnan People's Republic of China.
  • Hu QF; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, Yunnan People's Republic of China.
  • Yang GY; Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industrial Co., Ltd , Kunming 650231, Yunnan People's Republic of China.
Org Lett ; 19(18): 4952-4955, 2017 09 15.
Article en En | MEDLINE | ID: mdl-28876077
Phytochemical investigation on Lepidium meyenii led to the discovery of macahydantoin C (3), a new thiohydantoin with a 1,3-diazabicyclo[3.3.1]nonane core, the spectral properties of which indicate a potential structural misassignment of its previously reported analogue, macahydantoin B (2a). To probe this hypothesis, a concise, scalable, and biomimetic synthesis of the originally proposed 2a and its revised structure (2b) was efficiently accomplished using the modified Edman degradation as the key step from commercially available materials in 65% (three steps) and 52% (three steps) overall yields, respectively. These synthetic endeavors undoubtedly reassigned the structure of macahydantoin B as an unreported type of thiohydantoin featuring a 4-methyl-hexahydropyrrolo[1,2-c]imidazole scaffold.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Lepidium Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2017 Tipo del documento: Article

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Lepidium Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2017 Tipo del documento: Article
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