Catalytic enantioselective total synthesis of (−)-ar-Tenuifolene

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

“…Without isolation of the intermediate, the protecting group was removed and the product was obtained in 88% yield and 80% ee. The enantiomeric excess of the ob-Scheme 16: Usage of a Michael addition catalysed by L9/Pd(TFA) 2 in the total synthesis of (-)-ar-tenuifolene [12].…”

“…The catalytic system L9/Pd(TFA) 2 was further used in the work published in 2020 by Bisai et al for the addition of 4-tolylboronic acid to 3-methyl-2-cyclohexenone in the total synthesis of the aromatic sesquiterpene (−)-ar-tenuifolene (Scheme 16) [12].…”

“…The asymmetric 1,4-addition of arylboronic acids to conjugated cyclic enones and chromones is a very important reaction nowadays. For illustration, the addition products are very promising in medicinal chemistry research [1][2][3][4][5][6][7] and in natural products total syntheses [8][9][10][11][12][13][14][15][16]. Chiral complexes of Rh [17][18][19][20][21][22][23][24] and Pd usually catalyse the reaction, however, palladium holds a special place in this area.…”

Penispidins A–C, Aromatic Sesquiterpenoids from Penicillium virgatum and Their Inhibitory Effects on Hepatic Lipid Accumulation

“…Only a few related compounds have been reported, which were all isolated from plants. Specifically, two dunniane-type examples were isolated from Illicium dunnianum in 1998 and from Cupressus macrocarpa foliage in 2005; , eight 7,12-cyclized bisabolane-type representatives were reported from Laurencia majuscule in 1992 and Osyris tenuifolia in 2004 (Scheme 1, Supporting Information). , However, they have attracted significant attention from synthetic chemists due to their unique structures, − although their bioactivities remain hitherto unknown.…”