Chemoenzymatic syntheses of the linear triquinane-type sesquiterpenes (+)-hirsutic acid and (−)-complicatic acid

Natural sesquiterpenoids

“…210 Chemoenzymatic syntheses of (+)-hirsutic acid and (−)-complicatic acid have been achieved. 211 Rapraesentins D-F 214-216 and 1,2-dehydrolactarolide A 217 are new plant growth regulators, which have been isolated from the fungi Lactarius repraesentaneus 212 and Lactarius vellereus, 213 respectively. A group of lactarene derivatives have been tested as antiviral, cytotoxic, antiproliferative and immunotropic agents.…”

Corrosion News

“…Further routes to (±)‐coriolin ( 113 ) starting from trimethylated bicyclo[2.2.2]octenediones were reported by Singh et al 167a,b,h. Other linear triquinanes that have been synthesized using an oxa‐di‐π‐methane rearrangement as the key step are (±)‐Δ 9(12) ‐capnellene,167c, 168 (−)‐phellodonic acid,169a (±)‐167d,e and (−)‐hirsutene,169b,c (±)‐167f and (−)‐complicatic acid,169d,e and finally (±)‐167f,g and (+)‐hirsutic acid ( 114 ),169d,e which will be discussed later in this section.…”

“…used reactive dienes that were generated by the Adler reaction of salicyl alcohols, Banwell and co‐workers employed enantiomerically pure dienes, which were obtained by microbial dihydroxylation of toluene. To allow comparison, some of the intermediates that were produced during the total syntheses of (+)‐169d,e and (±)‐hirsutic acid167f,g ( 114 , Figure 4) are depicted in Scheme , namely the primary Diels–Alder cycloaddition products 122 and 125 , as well as the substrates ( 123 and 126 ) and products ( 124 and 127 ) of the oxa‐di‐π‐methane rearrangement.…”

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

“…Chlorostereone (26) and complicatic acid (27) have been isolated from strain IBWF01082 of Stereum, and they probably share the same biosynthetic pathway [20]. Chlorostereone (26) showed cytotoxicity against Jurkat cells with an IC 50 value of 5 µg mL −1 . Complicatic acid (27) was first obtained in 1973 from Stereum complicatum, and it showed broad but moderate biological activities against numbers of microorganisms including bacteria and certain fungi [21].…”