56968-75-3Relevant academic research and scientific papers
Stereo- and regiocontrolled hydroxylation of oxyallyl [4+3] cycloadducts. A concise synthesis of hinokitiol
Lee, Jae Chol,Cho, Sung Yun,Cha, Jin Kun
, p. 7675 - 7678 (1999)
Stereo- and regioselective hydroxylation of 8-oxabicyclo[3.2.1]oct-6-en-3-ones was achieved by the action of (diacetoxyiodo)benzene in methanolic potassium hydroxide (the Moriarty oxidation). Subsequent double elimination afforded a convenient preparation of substituted tropolones, as exemplified in a three-step synthesis of hinokitiol (1).
The Palladium-Mediated Cross Coupling of Bromotropolones with Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogues
Banwell, Martin G.,Cameron, Jennifer M.,Collis, Maree P.,Crisp, Geoffrey T.,Gable, Robert W.,'et al.
, p. 705 - 728 (2007/10/02)
The bromotropolones (4), (5) and (10) undergo palladium-mediated cross coupling with a wide range of organostannanes to produce alkenyl-, alkyl- and aryl-substituted tropolones.The methodology has been applied to the synthesis of the monoterpenes β-dolabrin (11), β-thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and β-thujaplicinol (14).Cross coupling of bromotropolones (4), (5) and (10) with various aryltrimethylstannanes or arylboronic acids has permitted the preparation of the bicyclic colchicine analogues (30)-(43) which have been tested for tubulin-binding activity.The X-ray crystal structure of the most active of these systems, compound (38), is reported.
The Palladium-mediated Cross-coupling of Bromotropolones with Organostannanes; Application to Concise Syntheses of β-Dolabrin, β-Thujaplicin, 7-Methoxy-4-isopropyltropolone, and β-Thujaplicinol
Banwell, Martin G.,Collis, Maree P.,Crisp, Geoffrey T.,Lambert, John N.,Reum, Monica E.,Scoble, Judith A.
, p. 616 - 617 (2007/10/02)
The bromotropolones (1), (2), and (3) cross-couple with organostannanes in the presence of palladium(O) to produce alkyl, alkenyl, or aryl substituted tropolones; the methodology has been applied to the synthesis of the monoterpenes β-dolabrin (4), β-thujaplicin (5), 7-methoxy-4-isopropyltropolone (7), and β-thujaplicinol (8).
