(-)-Lytophilippine A: synthesis of a C1-C18 building block.
The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing d-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).
Gille
Annika
A
Fakultät Chemie, Technische Universität Dortmund, 44227 Dortmund, Germany. annika.gille@tu-dortmund.de
Hiersemann
Martin
M
D000818:Animals; D002384:Catalysis; D005690:Galactose / Q000737:chemistry; D037402:Hydrozoa / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D018942:Macrolides; C554886:lytophilippine A; D005690:Galactose