351186-81-7Relevant articles and documents
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.
A general strategy for the convergent synthesis of fused polycyclic ethers via B-alkyl Suzuki coupling: Synthesis of the ABCD ring fragment of ciguatoxins
Sasaki, Makoto,Ishikawa, Makoto,Fuwa, Haruhiko,Tachibana, Kazuo
, p. 1889 - 1911 (2007/10/03)
A new method for convergent coupling of fused polycyclic ethers has been developed, which relies on B-alkyl Suzuki crosscoupling of lactone-derived enol triflates or phosphates. The strategy was successfully applied to a convergent synthesis of the ABCD r
A general method for convergent synthesis of polycyclic ethers based on Suzuki cross-coupling: Concise synthesis of the ABCD ring system of ciguatoxin
Sasaki, Makoto,Fuwa, Haruhiko,Ishikawa, Makoto,Tachibana, Kazuo
, p. 1075 - 1077 (2008/02/09)
(matrix presented) A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupli