1028432-87-2Relevant academic research and scientific papers
Total synthesis of (-)-brevenal: A streamlined strategy for practical synthesis of polycyclic ethers
Ebine, Makoto,Fuwa, Haruhiko,Sasaki, Makoto
, p. 13754 - 13761 (2012/01/06)
We describe a streamlined strategy for the practical synthesis of trans-fused polycyclic ethers and its application to a concise total synthesis of (-)-brevenal, a new pentacyclic polyether natural product with intriguing biological activities. The B-, D-, and E-rings were constructed by TEMPO/PhI(OAc)2-mediated oxidative lactonization of the corresponding 1,6-diols, with minimal need for manipulation of oxygen functionalities. The B- and E-ring lactones were appropriately functionalized by Suzuki-Miyaura coupling of lactone-derived enol phosphates and subsequent stereoselective hydroboration. The A-ring was formed by our mixed thioacetalization methodology. The AB- and DE-ring fragments were assembled through Suzuki-Miyaura coupling, and the C-ring was forged in the same manner as that for the A-ring. More than two grams of the pentacyclic polyether core of (-)-brevenal have been synthesized by the synthetic route developed in this study.
Total synthesis of (-)-brevenal: A concise synthetic entry to the pentacyclic polyether core
Ebine, Makoto,Fuwa, Haruhiko,Sasaki, Makoto
supporting information; experimental part, p. 2275 - 2278 (2009/05/11)
(Chemical Equation Presented) 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-
