Concise synthesis of the multiply oxygenated ABC-ring system of the dihydro-β-agarofurans.
The multiply oxygenated ABC-ring system of the dihydro-β-agarofurans was synthesized by employing two highly stereoselective reactions. The quinidine-catalyzed Diels-Alder reaction between a chiral dienophile and 3-hydroxy-4-methyl-2-pyrone simultaneously installed the C2-stereogenic center and two contiguous tetrasubstituted carbon centers (C5 and C10) of the A-ring. After 12 additional transformations, the aldol reaction of the resulting spiral AC-ring cyclized the B-ring with stereoselective introduction of the C7- and C8-centers.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.
Tomochika
T
Ishiyama
Daisuke
D
Urabe
Hiroki
H
Fujisawa
Masayuki
M
Inoue
D029753:Celastraceae / Q000737:chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D011802:Quinidine / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011753:Pyrones; D012717:Sesquiterpenes; C008316:maltol; D011802:Quinidine