Total synthesis of applanatumols X and Y

Insights into Ganoderma fungi meroterpenoids opening a new era of racemic natural products in mushrooms

“…124 The first total synthesis of (±)-lingzhilactone B (101 and 102) was accomplished by the Qin goup in 11 steps and 9% overall yield via semipinacol rearrangement. 125 And in 2020, they developed a collective strategy for the concise synthesis of (+)-lingzhilactones B and C (101 and 119), (−)-lingzhiol (136), and (+)-sinensilactam A (687) in 13, 14, 10, and 14 steps, respectively, relying on the divergent reactivity of styrene. 126 Lingzhilactone B and its structurally similar meroterpenoids applanatumol F ( 121) and (±)-sinensilactam A (687 and 688) were also achieved by the Yang group in 2018, relying on an intramolecular rhodium-catalyzed [3+2] cycloaddition and a convergent and tandem condensation.…”

“…127 Enantiomers of (±)-lingzhiol (135 and 136) have attracted much attention. Its first total synthesis was reported by the Yang group in 2014 that (−)-lingzhiol (136) was achieved in 17 steps exploiting a rhodium-catalyzed [3+2] cycloaddition. 128 In 2015, the Qin group developed an eight-steps chemical strategy to syntheses (±)-lingzhiol (135 and 136) by using a one-step construction to get a 5/5/6/6 ring system with the overall yield of 7.8%.…”

Structural diversity, hypothetical biosynthesis, chemical synthesis, and biological activity ofGanodermameroterpenoids

“…Next, reduction of malonate and the ketone moiety Ito ′ s group used the key intermediate 209 in the synthesis of applanatumol B (207) to accomplish the total synthesis of applanatumols X and Y in 9 and 10 steps. 97,99 Compound 209 was prepared from 2,5-dimethoxybenzaldehyde (209) and 4pentyn-1-ol (208) in ve steps including an intramolecular Morita-Baylis-Hillman reaction to build the ve-membered ring. Finally, the total synthesis of applanatumols X (210) and Y (211) was completed (Fig.…”

Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[b]chromenocarbonitrile Derivatives

“…P133 and possess antituberculosis activity against the virulent strain of Mycobacterium tuberculosis . Applanatumol Y was isolated by Cheng in 2016 from the fruiting body of Ganoderma applanatum, which is a wood-decaying fungi . Total synthesis of this compound was performed by Ito using a Morita–Baylis–Hillman reaction as a key step .…”