Progress toward the Synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core.
[reaction: see text] A highly diastereoselective single-step cyclization reaction provides access to the bicyclo[3.3.1]nonane core of the polyprenylated phloroglucin natural product garsubellin A. Further elaboration to a more functionalized analogue involves a sequential Claisen rearrangement/Grubbs olefin cross-metathesis strategy. Additionally, this strategy was extended to the preparation of the bis-quaternary carbon array found at the bridgehead positions of the phloroglucin natural products.
Spessard
Sarah J
SJ
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Stoltz
Brian M
BM
D000544:Alzheimer Disease / Q000188:drug therapy; D002795:Choline O-Acetyltransferase / Q000378:metabolism*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D018696:Neuroprotective Agents / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D018696:Neuroprotective Agents; D010456:Peptides, Cyclic; D013729:Terpenes; C106690:garsubellin A; C458300:lobocyclamide B; D002795:Choline O-Acetyltransferase