Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp

Org Lett. 2002 Sep 19;4(19):3223-6. doi: 10.1021/ol026421y.

Abstract

[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.

MeSH terms

  • Animals
  • Biological Factors / chemical synthesis*
  • Biological Factors / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Propylene Glycols / chemical synthesis*
  • Propylene Glycols / chemistry*
  • Urochordata / chemistry*

Substances

  • Biological Factors
  • Propylene Glycols
  • didemniserinolipid B