938455-98-2Relevant academic research and scientific papers
Convergent synthesis of the BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ethers
Sato, Kazushi,Sasaki, Makoto
, p. 5977 - 6003 (2008/02/07)
A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring.
Studies toward the total synthesis of gambieric acids A and C: Convergent assembly of the nonacyclic polyether skeleton
Sato, Kazushi,Sasaki, Makoto
, p. 2518 - 2522 (2008/03/11)
(Chemical Equation Presented) A solid approach to ethereal rings: Key features of a convergent synthesis of the nonacyclic polyether skeleton of gambieric acids A and C include the connection of the BCD and GHIJ ring systems by esterification, the construction of the E ring in the form of a lactone, a stereoselective allylation to establish the C26 stereocenter, and the formation of the F ring by ring-closing metathesis (see scheme; Bn = benzyl, NAP = 2-naphthylmethyl).
