First stereoselective total synthesis of FD-594 aglycon.
Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular S(N)Ar reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI(2)-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.
Masuo
Ritsuki
R
Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
Ohmori
Ken
K
Hintermann
Lukas
L
Yoshida
Saki
S
Suzuki
Keisuke
K
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
D000903:Antibiotics, Antineoplastic; C112184:FD 594, antibiotic; D007783:Lactones; D011714:Pyrans; D014966:Xanthenes