Total synthesis of the chlorinated marine natural product dysamide B.
[Structure: see text] Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha,alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.
Durow
Amanda C
AC
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
Long
G Cliona
GC
O'Connell
Susan J
SJ
Willis
Christine L
CL
D000818:Animals; D047088:Dysidea / Q000378:metabolism; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000378:metabolism; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000378:metabolism
D006843:Hydrocarbons, Chlorinated; D010879:Piperazines; C517077:dysamide B