Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.
[structure: see text] En route to proving the absolute and relative stereochemistry, through synthesis, of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., it was discovered that the isolated natural product was in fact the 31-sulfate configured 8R,9R,10R,13S,30S. This structural reassignment was only possible after the development of a microwave-assisted method for the sulfation of unreactive hydroxyl groups.
Kiyota
Hiromasa
H
Department of Chemistry, University of Cambridge, UK.
Dixon
Darren J
DJ
Luscombe
Christine K
CK
Hettstedt
Stephan
S
Ley
Steven V
SV
D000818:Animals; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry*; D014561:Urochordata / Q000737:chemistry*
D001685:Biological Factors; D011409:Propylene Glycols; C467921:didemniserinolipid B