scholarly journals Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C–H/C–H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

2021 ◽  
Author(s):  
Zhe Zhuang ◽  
Alastair N. Herron ◽  
Shuang Liu ◽  
Jin-Quan Yu
Keyword(s):  
Total Synthesis ◽  
Rapid Construction

Synthetic Studies towards the Total Synthesis of Indole Alkaloids Containing Indolyl Lactam Frameworks

Synlett ◽  
2020 ◽  
Author(s):  
Fu-She Han ◽  
Dong-Xing Tan
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Cycloaddition Reaction ◽  
Terminal Olefin ◽  
Asymmetric Reaction ◽  
Rapid Construction ◽  
Fused Ring ◽  
Acid Catalyzed ◽  
Synthetic Studies ◽  
Type Substitution

AbstractIn this account, recent progress on the synthetic studies of several monoterpene indole alkaloids, (±)-mersicarpine, misassigned (±)-tronoharine, and (±)-leuconodines D and E, is summarized. Specifically, the rationale for the design and development of the Lewis acid catalyzed SN1-type substitution and formal [3+3] cycloaddition reaction of indol-2-yl carbinols, and the Pd-catalyzed aerobic oxidative intramolecular Heck cross-coupling of indolyl amides tethered with a terminal olefin functionality, are emphasized. These key reactions set the basis for the rapid construction of the fused ring skeleton containing an all-carbon quaternary center at the indol-2-yl position.1 Introduction2 Synthetic Study of (±)-Mersicarpine3 Synthetic Study of the Misassigned (±)-Tronoharine4 Study of the Asymmetric Reaction of Indol-2-yl Carbinols5 Synthetic Study of (±)-Leuconodines D and E6 Conclusion

scholarly journals Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C−H/C−H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

2020 ◽  
Author(s):  
Zhe Zhuang ◽  
Alastair Herron ◽  
Shuang Liu ◽  
jin-quan yu
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Phenylacetic Acid ◽  
Coupling Reaction ◽  
Pivalic Acid ◽  
Coupling Reactions ◽  
Amino Acid Ligand ◽  
Acid Ligand ◽  
Rapid Construction ◽  
Synthetic Application

The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp<sup>3</sup>)−H/C(sp<sup>2</sup>)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-<i>N</i>-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.

scholarly journals Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)-Clavosolide A

2016 ◽  
Vol 128 (7) ◽  
pp. 2544-2548 ◽  
Author(s):  
Alba Millán ◽  
James R. Smith ◽  
Jack L.-Y. Chen ◽  
Varinder K. Aggarwal
Keyword(s):  
Total Synthesis ◽  
Prins Reaction ◽  
Rapid Construction

General One-Pot Reductivegem-Bis-Alkylation of Tertiary Lactams/Amides: Rapid Construction of 1-Azaspirocycles and Formal Total Synthesis of (±)-Cephalotaxine

2013 ◽  
Vol 19 (39) ◽  
pp. 13075-13086 ◽  
Author(s):  
Kai-Jiong Xiao ◽  
Jie-Min Luo ◽  
Xiao-Er Xia ◽  
Yu Wang ◽  
Pei-Qiang Huang
Keyword(s):  
Total Synthesis ◽  
One Pot ◽  
Rapid Construction

scholarly journals Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C−H/C−H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

2020 ◽  
Author(s):  
Zhe Zhuang ◽  
Alastair Herron ◽  
Shuang Liu ◽  
jin-quan yu
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Phenylacetic Acid ◽  
Coupling Reaction ◽  
Pivalic Acid ◽  
Coupling Reactions ◽  
Amino Acid Ligand ◽  
Acid Ligand ◽  
Rapid Construction ◽  
Synthetic Application

The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp<sup>3</sup>)−H/C(sp<sup>2</sup>)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-<i>N</i>-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.

The total synthesis of (±)-petasitolone

1984 ◽  
Vol 62 (12) ◽  
pp. 2676-2681 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Teng Ko Ngooi
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Good Yield ◽  
Ring System ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
Target Molecule ◽  
Rapid Construction ◽  
Excellent Control ◽  
Acid Catalyzed

The total synthesis of petasitolone (1), a sesquiterpenoid of the eremophilane family, has been accomplished. The key step of this efficient synthesis is the Lewis acid catalyzed Diels–Alder addition of 2-carbomethoxy-2-cyclohexenone (3) to diene 9. The cycloaddition, which gives adduct 16 in good yield, facilitates the rapid construction of the parent ring system of the target molecule and allows an excellent control of the required stereochemistry.

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