Total Synthesis of Neolaulimalide and Isolaulimalide
Organic Letters2008Vol. 10(20), pp. 4701–4704
Citations Over TimeTop 14% of 2008 papers
Abstract
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).
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