151073-98-2Relevant academic research and scientific papers
Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclizations to prepare highly functionalized seven-membered cyclic ethers
Berger, Daniel,Overman, Larry E.,Renhowe, Paul A.
, p. 2446 - 2452 (2007/10/03)
The first synthesis of the title compound is described. The synthesis features an acetal-vinylsilane cyclization to stereoselectively form the cis-2,7-disubstituted oxepene ring and introduce Δ4 unsaturation. Starting with (2R,3S)-2,3-epoxypentan-1-ol (16), mixed acetal 10 is formed in five steps and 72% overall yield. Treatment of 10 with excess BC13 in CH2Cl2 at -78 → 0°C promotes cyclization to afford Δ4-oxepene 39 in 90% yield after deprotection of the silyl ether. Elaboration of the (E)-enyne functionality of the six-carbon side chain completes the synthesis of (±)-isolaurepinnacin.
