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.

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.

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 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.

ChemInform Abstract: Olefin Metathesis Based Approach to Diversely Functionalized Pyrrolidizidines and Indolizidines; Total Synthesis of (+)-Monomorine.

ChemInform ◽  
2009 ◽  
Vol 40 (21) ◽  
Author(s):  
Giordano Lesma ◽  
Alessia Colombo ◽  
Alessandro Sacchetti ◽  
Alessandra Silvani
Keyword(s):  
Total Synthesis ◽  
Olefin Metathesis

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
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