Synthesis of the A-B subunit of angelmicin B.
[reaction: see text] An efficient synthesis of the tricyclic A-B subunit 2 of angelmicin B is described. A formal three-component coupling of aldehydes 4 and 6 with gamma-silylallylborane 7 was employed to assemble the tetrahydrofuranyl core of 2, a strategy highlighted by the stereoselective [3 + 2] annulation of allylsilanes 5a/5b with aldehyde 4. The efficiency of the [3 + 2] annulation was greatly improved by using the allylic benzhydryldimethylsilane 5b compared to the allylic phenyldimethylsilane 5a.
Lambert
William T
WT
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Roush
William R
WR
D000447:Aldehydes / Q000737:chemistry; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000880:Anthraquinones; D001896:Boron Compounds; D017646:Organosilicon Compounds; C083655:angelmicin B