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Synfacts 2011(3): 0238-0238  
DOI: 10.1055/s-0030-1259409
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Nakadomarin

Contributor(s): Steven V. Ley, James R. Frost
M. G. Nilson, R. L. Funk*
The Pennsylvania State University, University Park, USA
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

(-)-Nakadomarin A was isolated by Kobayashi in 1997 from the Okinawan sponge ­Amphimedon sp. and has attracted much attention owing to its intriguing structure. However, completion of the fifteen-membered macrocycle has generally proven difficult, with the undesired E-olefin configuration often observed. The Funk group rectifies this problem with the use of alkyne metathesis followed by Lindlar reduction to give a single Z-isomer.