Synthesis of (-)-Nakadomarin

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.