Total synthesis of (±) mutisianthol and (±) epi-mutisianthol via intramolecular oxidative Heck cyclization approach

Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine

“…Moreover, no indene sideproducts are detected in the crude product mixture using 1 H-NMR analysis. An investigation of the inuence of solvents on the ATH reaction of 1s (entries [11][12][13][14][15][16][17] shows that reactions in the CH 3 CN, CH 2 Cl 2 , THF and EtOAc produce cis-indanol 2s in high ee (99% ee), but that the conversion of 1s to 2s is less than 50% aer 6 h and the % ee of the recovered indanone 1s is not high (36-83% ee). However, reaction in MeOH for 6 h using 1 : 5 FA/TEA and C3 as the catalyst (entry 17) leads to reduction of only (3R)-1s to form (1R,3R)-2s (50%, 99% ee) and recovery of unreacted (3S)-1s (50%, 99% ee).…”

“…13 An example of a bioactive indane bearing a 3-alkenyl group is (+)-multisianthol, which has antitumor activity. 14,15 In addition, 3-arylindanoles and 3-arylindanones are valuable intermediates in routes for the synthesis medicinal agents.…”

Intramolecular Heck Reaction in Total Synthesis of Natural Products: An Update

“…In 2016, Bhorkade et al [47] . reported the total synthesis of sesquiterpene mutisianthol ( 159 ) where Heck cyclization was used first time to make the indane scaffold.…”

“…In 2016, Bhorkade et al [47] reported the total synthesis of sesquiterpene mutisianthol (159) where Heck cyclization was used first time to make the indane scaffold. During their synthesis Heck precursor 157 was treated with (Ph 3 P) 4 Pd, Et 3 N, LiCl in DMF to make the key indane derivative 158 in an excellent yield (Scheme 16).…”

Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5-Endo-Trig Cyclization

“…For example, trans -trikentrin A bearing an alkylated indane has good antimicrobial activity, whereas ramelteon is used for the treatment of insomnia . Moreover, (+)-multisianthol bearing an alkenyl group was reported to have antitumor activity . Other examples of bioactive indanes containing aryl substituents include (+)-indatraline for the treatment of depression and cocaine addiction, (+)-isopaucifloral F with antiosteoporosis activities, (+)-pallidol possessing estrogen-like properties, and α-diisoeugenol, which is cytotoxic (Scheme ).…”