Total synthesis of (-)-ecklonialactone B.
The total synthesis of (-)-ecklonialactone B as well as the 9,10-dihydro derivative by two different strategies is reported. The catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers delivered elaborated α-keto ester building blocks. Ring-closing metatheses, including a notable diastereotopos-differentiating variant, a B-alkyl Suzuki-Miyaura cross-coupling reaction and a regio- and diastereoselective last-step epoxidation are key contributors.
Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund , 44227 Dortmund, Germany.
Julia
J
Becker
Lena
L
Butt
Valeska
V
von Kiedrowski
Elisabeth
E
Mischler
Florian
F
Quentin
Martin
M
Hiersemann
D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C086785:ecklonialactone B