The total synthesis of spectinabilin and its biomimetic conversion to SNF4435C and SNF4435D

Organic Letters

Volumn 7, Issue 12, 2005, Pages 2473-2476

  Jacobsen, Mikkel F ^a   Moses, John E ^a   Adlington, Robert M ^a   Baldwin, Jack E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOSUPPRESSIVE AGENT; SNF 4435 C; SNF 4435 D; SPECTINABILIN; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; DRUG SYNTHESIS; METHYLATION; SUZUKI REACTION;

MOLECULAR MIMICRY; MOLECULAR STRUCTURE; NITRO COMPOUNDS; PYRONES; STEREOISOMERISM;

EID: 20544470969     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0507874     Document Type: Article

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25. We are grateful for an authentic sample of (-)-spectinabilin (3) donated by Dr. M. Isaka, National Center for Genetic Engineering and Biotechnology, Klong Luang, Pathumthani 12120, Thailand.
26. See the Supporting Information.
27. 1H NMR. The same is true for the C10-C11 double bond in aureothin (4). Prolonged exposure of 3 to light leads to a complex product mixture.
28. 1 and 2 could be separated by preparative TLC, see the Supporting Information.
29. 2. The structure of 14 and 15 was unambiguously confirmed by NMR, IR, and HRMS; see the Supporting Information.
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