The first total synthesis of Gardneria oxindole alkaloid (−)-gardmultimine A has been achieved in 19 steps from d-tryptophan in a fully stereocontrolled manner. This synthesis features (1) an Ir-catalyzed regioselective C–H borylation/oxidation sequence to introduce the C12 methoxyl group, (2) a stereocontrolled oxidative rearrangement of indole to construct the spirooxindole motif, and (3) an Au­(I)-catalyzed transannular Conia-ene-type 6-exo-dig cyclization to establish the azabicyclo[2.2.2]­octane skeleton and the exocyclic E-alkene with exclusive stereoselectivity.

The skeleton of lucidumone was constructed through oxidative dearomatization/intramolecular Diels−Alder reaction, Cu-mediated remote C−H hydroxylation, allyl oxidation, acid-promoted dynamic kinetic resolution cyclization, and benzylic oxidation.M eroterpenoids are important natural products and widely present in plants and fungi. So far, many meroterpenoids have been isolated. Among these natural products, meroterpenoids isolated from fungi mainly have complex diverse structures and potent biological characteristics, which have attracted a great deal of attention from the pharmacological and synthetic communities. 1 So far, many kinds of meroterpenoids have been isolated from Ganoderma mushrooms, bearing complex structures and potent biological activities. 2 Recently, several Ganoderma meroterpenoids were isolated, including lingzhiol, 3 applanatumol C, 4 sinensilactam A, 5 applanatumol B, 6 and cochlearol A 7 (Figure 1).In 2019, a novel meroterpenoid named lucidumone was isolated from the fruiting bodies of Ganoderma lucidum. 8 Related investigations showed that it can selectively inhibit COX-2 via binding to Tyr385. 9

The first total syntheses of (±)-catellatolactams A and B, two novel ansamacrolactams, are described in 5 and 8 steps, respectively. The strategy relies on an amidation reaction to couple the acylated Meldrum's acid and an aryl amine, a regioselective C− H insertion to construct the γ-lactam moiety, and an RCM reaction to forge the macrocycles with E-olefin. This concise and scalable synthesis provided over 200 mg of the target molecules.Letter pubs.acs.org/OrgLett

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A strategy for the synthesis of cis-hydrocarbazole with a C3 quaternary carbon center has been developed through nickel/Lewis acid dual-catalyzed arylcyanation. A wide array of cis-hydrocarbazoles was accessed with high diastereoselectivities and atom economies in a good yield. The rich chemistry of the installed nitrile group was demonstrated in the preparation of tryptamine- and tryptophol-derived cis-hydrocarbazoles.