Total synthesis of neolaulimalide and isolaulimalide.
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).
Gollner
Andreas
A
Institut für Organische Chemie, Universität Wien, Währingerstrasse 38, 1090 Vienna, Austria.
Mulzer
Johann
J
D015394:Molecular Structure; D043823:Taxoids / Q000138:chemical synthesis* / Q000737:chemistry
D043823:Taxoids; C117306:isolaulimalide; C533382:neolaulimalide