Total synthesis of (-)-brevenal: a concise synthetic entry to the pentacyclic polyether core.
Total synthesis of (-)-brevenal, a novel marine polycyclic ether natural product, is described. Highly efficient and scalable entries to the AB-ring exo-olefin and the DE-ring enol phosphate and a rapid construction of the C-ring by means of our Suzuki-Miyaura coupling-based strategy realized a concise synthesis of the pentacyclic skeleton of (-)-brevenal. The present synthesis is considerably more efficient than our previous synthesis (longest linear sequence: 50 steps from 2-deoxy-d-ribose).
Ebine
Makoto
M
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Sendai, Japan.
Fuwa
Haruhiko
H
Sasaki
Makoto
M
D004987:Ethers / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism; D013874:Thiopental / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013997:Time Factors
D004987:Ethers; D011108:Polymers; C004316:thiobutabarbital; D013874:Thiopental