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Molecules 2010, 15(12), 8784-8795; doi:10.3390/molecules15128784
Article

Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue

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Received: 4 November 2010 / Revised: 25 November 2010 / Accepted: 29 November 2010 / Published: 2 December 2010
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Abstract

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.
Keywords: psammaplin F; marine bromotyrosine; Cleland’s reagent; total synthesis; X-ray crystal structure psammaplin F; marine bromotyrosine; Cleland’s reagent; total synthesis; X-ray crystal structure
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Yang, Q.; Liu, D.; Sun, D.; Yang, S.; Hu, G.; Wu, Z.; Zhao, L. Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue. Molecules 2010, 15, 8784-8795.

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