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Total Synthesis of Neolaulimalide and Isolaulimalide

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journal contribution
posted on 16.10.2008, 00:00 by Andreas Gollner, Johann Mulzer
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).