Journal
MOLECULES
Volume 15, Issue 12, Pages 8784-8795Publisher
MDPI
DOI: 10.3390/molecules15128784
Keywords
psammaplin F; marine bromotyrosine; Cleland's reagent; total synthesis; X-ray crystal structure
Funding
- China International Science and Technology Cooperation Plan [2009DEA31200]
- National Science and Technology Key Specific Project for Significant Creation of New Drugs [2009ZX09301-012]
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Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland's reagent reduction as key step. The longest linear synthetic sequence starting from 3-bromo-4-hydroxybenzaldehyde and hydantoin was seven steps. In addition, a detailed X-ray crystal structure analysis of psammaplin A analogue 8b is given for the first time.
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