Total Synthesis of Neolaulimalide and Isolaulimalide

Andreas Gollner and Johann Mulzer*

Organic Letters (2008), 10(20), 4701-4704. 

The first total syntheses of the potential antitumoral leads neolaulimalide (2) and isolaulimalide (3) have been achieved. Key steps in our convergent, fully stereocontrolled route are a Yamaguchi macrolactonization, a Julia−Lythgoe−Kocienski olefination, a Kulinkovich reaction, and a cyclopropyl−allyl rearrangement to install the exo-methylene group. Overall, we synthesized 2 in 21 linear steps (3% yield) and 3 in 24 steps (2% yield).