Short and efficient synthesis of (+)-subersic acids

Concise synthesis of (+)-subersic acid from (−)-Sclareol

“…They selected (À)-Sclareol as a starting material and gave (þ)-subersic acid in 14 steps with an overall yield of 4.3%. 5 All about this encouraged us to develop a short, practical and efficient route to achieve (þ)-subersic acid.…”

Natural product synthesis from (8aR)- and (8aS)-bicyclofarnesols: synthesis of (+)-wiedendiol A, (+)-norsesterterpene diene ester and (−)-subersic acid

“…5 Meanwhile, the synthesis of (+)-3 from the natural product sclareol was carried out via carbon-carbon bond formation at the dotted line b (Scheme 1) between an allyl bromide part, corresponding to the left-hand side of (À)-3, and an aryl part. 11 Our synthetic plan is shown in Scheme 4; this also involves carbon-carbon bond formation at the dotted line b. In this way we attempted to improve the coupling yield, since the yield in previous case 11 was 26%.…”

“…11 Our synthetic plan is shown in Scheme 4; this also involves carbon-carbon bond formation at the dotted line b. In this way we attempted to improve the coupling yield, since the yield in previous case 11 was 26%.…”

Synthesis of Isoprenyl Flavonoids: (+)-Denticulaflavonol, Macarangin, and Isomacarangin

“…Sclareol 12 was acetylated in quantitative yield with acetyl chloride and N,N-dimethylaniline affording the diacetyl derivative; the isomerisation of which with bis(acetonitrile)palladium (II) chloride 13 and elimination of the acetoxy group at C-8 12b gave the monoacetyl derivative 5. 14 The hydrolysis of the acetoxy group of 5 gave alcohol 6 in quantitative yield. Subsequent treatment with CBr 4 and Ph 3 P 15 led to the corresponding bromoderivative 7, also in quantitative yield.…”