An Efficient Synthetic Approach to the Aromatic Sesquiterpenoids via a Smi2-Promoted Construction of Quaternary Centre

2003 ◽  
Vol 2003 (2) ◽  
pp. 54-55 ◽  
Author(s):  
Xue Zhi Zhao ◽  
Yan Xing Jia ◽  
Yong Qiang Tu
Keyword(s):  
Total Synthesis ◽  
Synthetic Approach ◽  
Quaternary Carbon ◽  
Epoxy Alcohol

The total synthesis of the natural (±)-cuparene (1) and (±)-herbertene (2) has been carried out in eight steps from 2-cyclohexen-1-one (3) via a key quaternary carbon centre construction using a SmI2-promoted rearrangement of 2,3-epoxy alcohol.

scholarly journals A Synthetic Approach Toward a Brominated Oxocane Labdane Diterpenoid Isolated From Laurencia obtusa

2020 ◽  
Vol 15 (3) ◽  
pp. 1934578X2091286
Author(s):  
Hisahiro Hagiwara ◽  
Shohei Fujiwara ◽  
Chikako Iibachi ◽  
Toshio Suzuki ◽  
Takashi Hoshi
Keyword(s):  
Total Synthesis ◽  
Olefin Metathesis ◽  
Synthetic Approach ◽  
Epoxy Alcohol ◽  
Labdane Diterpenoid

The synthesis of a labdane oxocane epoxy-alcohol is described starting from the Wieland–Miescher ketone derivative via ring closing olefin metathesis of a diene derivative, targeting the total synthesis of a brominated oxocane labdane diterpenoid isolated from Laurencia obtusa.

scholarly journals Synthesis of Cyclohexane-Angularly-Fused Triquinanes

Synthesis ◽  
2020 ◽  
Author(s):  
Hongjun Jeon ◽  
Jeffrey D. Winkler
Keyword(s):  
Total Synthesis ◽  
Synthetic Approach ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Naturally Occurring

AbstractCyclohexane-angularly-fused triquinanes, 6-5-5-5 tetra­cycles, have attracted the attention of synthetic chemists due to their highly congested core structures and multiple quaternary carbon centers. This review focuses on the six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes in addition to seven notable methodologies that have been developed for the synthesis of these structures.1 Introduction2 6-5-5-5 Tetracycles Containing a Linear Triquinane2.1 Total Synthesis of Cyclopiane Diterpenes2.2 Synthetic Approach toward Aberrarane Diterpenes2.3 Intermediates in the Total Synthesis of Magellanine-Type Alkaloids3 6-5-5-5 Tetracycles Containing an Angular Triquinane3.1 Total Synthesis of Waihoensene3.2 Miscellaneous Approaches4 Conclusion

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

scholarly journals Recent development and applications of semipinacol rearrangement reactions

2021 ◽  
Author(s):  
Xiao-Ming Zhang ◽  
Bao-Sheng Li ◽  
Shao-Hua Wang ◽  
Kun Zhang ◽  
Fu-Min Zhang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Carbon Formation ◽  
Semipinacol Rearrangement ◽  
Rearrangement Reactions

The recent development of semipinacol rearrangement is reviewed, highlighting its application in β-functionalized ketone synthesis, quaternary carbon formation and total synthesis.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

scholarly journals Revision of the Structure and Total Synthesis of Topsentin C

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2562-2574 ◽  
Author(s):  
Nikita Golantsov ◽  
Alexey Festa ◽  
Alexey Varlamov ◽  
Leonid Voskressensky
Keyword(s):  
Total Synthesis ◽  
Secondary Metabolite ◽  
Conjugate Addition ◽  
Solvent Free ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Marine Alkaloids ◽  
Mild Reduction

An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.

Synthetic Approach Toward the Total Synthesis of Kempane Diterpenes via Transannular Diels−Alder Strategy

2006 ◽  
Vol 71 (19) ◽  
pp. 7370-7377 ◽  
Author(s):  
Franck Caussanel ◽  
Keyan Wang ◽  
Sreekanth A. Ramachandran ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Synthetic Approach

Bioinspired total synthesis of (−)-gymnothelignan L

2018 ◽  
Vol 5 (7) ◽  
pp. 1124-1128 ◽  
Author(s):  
Peng Chen ◽  
Liang Huo ◽  
Huilin Li ◽  
Lin Liu ◽  
Ziyun Yuan ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Asymmetric Total Synthesis

The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction.

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