Biomimetic total synthesis of litseaverticillols B, E, I, and J and structural reassignment of litseaverticillol E.
[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.
Vassilikogiannakis
Georgios
G
Department of Chemistry, University of Crete, 71409 Iraklion, Crete, Greece. vasil@chemistry.uoc.gr
Margaros
Ioannis
I
Montagnon
Tamsyn
T
D032701:Biomimetics / Q000379:methods*; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D026082:Singlet Oxygen / Q000737:chemistry; D013237:Stereoisomerism
D012717:Sesquiterpenes; C498385:litseaverticillol B; C498386:litseaverticillol E; C498387:litseaverticillol I; C498388:litseaverticillol J; D026082:Singlet Oxygen