Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols.
The construction of a highly functionalized adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols (PPAPs) is described. The method features the construction of the bicyclo[3.3.1]nonane core (3) by successive Michael reactions and the construction of the adamantane core of plukenetione-type PPAPs by acid-catalyzed cyclization of a bicyclo[3.3.1]nonane precursor (2).
Takagi
Ryukichi
R
Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan. rtakagi@hiroshima-u.ac.jp
Inoue
Yuta
Y
Ohkata
Katsuo
K
D000218:Adamantane / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D004987:Ethers / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D010696:Phloroglucinol / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*
D000473:Alkanes; D004987:Ethers; D011083:Polycyclic Compounds; C534123:plukenetione A; D010696:Phloroglucinol; D000218:Adamantane; C017573:nonane