Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers

Asymmetric total synthesis of the dimeric diterpenoid hispidanin A was accomplished by non‐catalytic Diels–Alder cycloaddition at room temperature. The synthesis relies on iron‐catalyzed coupling to construct a Z‐configured trisubstituted alkene, an iron‐catalyzed radical cascade to generate a labdane‐type diene, and both Yamamoto cationic polyene cyclization and palladium‐catalyzed Stille coupling to generate a totarane‐type dienophile.

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Asymmetric Total Synthesis of Hispidanin A

Deng

Cao

Liu

et al. 2017

Angewandte Chemie

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Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Wang

et al. 2022

Angewandte Chemie

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The asymmetric total synthesis of three lindenane sesquiterpenoid oligomers, shizukaol J, trichloranoid C and trishizukaol A, has been accomplished concisely in 15, 16 and 18 longest linear steps, respectively. The expeditious construction of molecular architectures was facilitated by Nelson's catalytic asymmetric ketene-aldehyde cycloaddition, a sequence of allylic alkylation/reduction/acidic cyclization to forge a lactone, and a double aldol condensation cascade to construct the 5/6 bicyclic system. Diastereoselective nucleophilic substitution promoted by a phase transfer catalyst constructed the C 11 quaternary stereogenic center, thus prompting synthetic efficacy toward shizukaol J. The synthesis of trichloranoid C and trishizukaol A was achieved after a cascade involving furanyl diene formation and a Diels-Alder reaction, as well as a one-pot sequence involving furan oxidation and global deprotection. Furthermore, our biological evaluation revealed that two compounds exhibited unexpected toxicity against tumor cell lines.

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Asymmetric Total Synthesis of Natural Lindenane Sesquiterpenoid Oligomers via a Triene as a Potential Biosynthetic Intermediate

Huang

Wang

et al. 2022

Angewandte Chemie

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A previously proposed triene of the lindenane skeleton was synthesized, characterized, and identified as the common intermediate for the non‐enzymatic synthesis of natural lindenane oligomers through linear, [4+2]‐type and [6+6]‐type homo‐ and hetero‐ dimerization under simulated physiological conditions. As a result, the following six natural products were successfully synthesized through thermal head‐to‐head, head‐to‐tail, and head‐to‐back binding modes: shizukaols A and J, cycloshizukaol A, chlorahupetone F, chlotrichene B, and trishizukaol A.

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Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers

Cited by 6 publications

References 41 publications

Asymmetric Total Synthesis of Hispidanin A

Asymmetric Total Synthesis of Hispidanin A

Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Asymmetric Total Synthesis of Natural Lindenane Sesquiterpenoid Oligomers via a Triene as a Potential Biosynthetic Intermediate

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