Biomimetic total synthesis of litseaverticillols B, E, I, and J and structural reassignment of litseaverticillol E

Org Lett. 2004 Jun 10;6(12):2039-42. doi: 10.1021/ol0493610.

Abstract

[reaction: see text] The first total synthesis of litseaverticillols B (1), E (2), I (4), and J (5) as well as the structural reassignment of litseaverticillol E (2) have been achieved by means of a biomimetic sequence of transformations during which a [4 + 2]-initiated reaction cascade and an ene reaction, both involving singlet oxygen ((1)O(2)), formed key steps. The reassignment of the structure of litseaverticillol E (3) to include an allylic hydroperoxide provides strong support for our biogenetic hypothesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetics / methods*
  • Molecular Conformation
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Singlet Oxygen / chemistry
  • Stereoisomerism

Substances

  • Sesquiterpenes
  • litseaverticillol B
  • litseaverticillol E
  • litseaverticillol I
  • litseaverticillol J
  • Singlet Oxygen