scholarly journals Total Synthesis and Structural Revision of a Harziane Diterpenoid

2019 ◽  
Author(s):  
Moritz Honig ◽  
Erick Carreira
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Spectral Characteristics ◽  
Tertiary Alcohol ◽  
Carbon Skeleton ◽  
Structural Revision ◽  
Stereochemical Analysis ◽  
Quaternary Stereocenter

The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.

Total Synthesis and Structural Revision of a Harziane Diterpenoid

2019 ◽  
Author(s):  
Moritz Honig ◽  
Erick Carreira
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Spectral Characteristics ◽  
Tertiary Alcohol ◽  
Carbon Skeleton ◽  
Structural Revision ◽  
Stereochemical Analysis ◽  
Quaternary Stereocenter

The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.

Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora

2015 ◽  
Vol 51 (28) ◽  
pp. 6202-6205 ◽  
Author(s):  
Matthew B. Calvert ◽  
Jonathan Sperry
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Synthetic Approach ◽  
Structural Revision ◽  
True Structure ◽  
Mimosa Tenuiflora

A bioinspired synthetic approach to nominal yuremamine has uncovered the true structure of the natural product to be a flavonoidal indole.

scholarly journals A Concise Total Synthesis of (±)-Vibralactone

2018 ◽  
Author(s):  
Sepand Nistanaki ◽  
Luke A. Boralsky ◽  
Roy D. Pan ◽  
Hosea Nelson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Early Stage ◽  
Ring Expansion ◽  
Biologically Active ◽  
Valence Isomerization ◽  
Reduction Strategy ◽  
Quaternary Stereocenter

Disclosed is a four-step synthesis of (<i>±</i>)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one forges both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone furnishes a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. Our concise and modular route to the natural product provides the shortest total synthesis of (<i>±</i>)-vibralactone reported to date. <br>

Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus

2018 ◽  
Vol 16 (27) ◽  
pp. 5043-5049 ◽  
Author(s):  
Yi Man ◽  
Shaomin Fu ◽  
Juan Chen ◽  
Bo Liu
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Total Synthesis ◽  
Structural Revision

Asymmetric total synthesis of compound 1, as a proposed molecular structure of a natural product, in 11 steps is described. The inconsistency of the characterization data prompted us to propose a different structure as compound 2 and accordingly accomplish total synthesis in 9 steps and confirm the structural revision of this natural product.

scholarly journals A Concise Total Synthesis of (±)-Vibralactone

2018 ◽  
Author(s):  
Sepand Nistanaki ◽  
Luke A. Boralsky ◽  
Roy D. Pan ◽  
Hosea Nelson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Early Stage ◽  
Ring Expansion ◽  
Biologically Active ◽  
Valence Isomerization ◽  
Reduction Strategy ◽  
Quaternary Stereocenter

Disclosed is a four-step synthesis of (<i>±</i>)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one forges both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone furnishes a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. Our concise and modular route to the natural product provides the shortest total synthesis of (<i>±</i>)-vibralactone reported to date. <br>

Total Synthesis and Structural Revision of Mycalol, an Anticancer Natural Product from the Marine Source

2015 ◽  
Vol 17 (7) ◽  
pp. 1652-1655 ◽  
Author(s):  
B. Seetharamsingh ◽  
P. R. Rajamohanan ◽  
D. Srinivasa Reddy
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Revision ◽  
Marine Source

scholarly journals A Concise Total Synthesis of (±)-Vibralactone

2018 ◽  
Author(s):  
Sepand Nistanaki ◽  
Luke A. Boralsky ◽  
Roy D. Pan ◽  
Hosea Nelson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Early Stage ◽  
Ring Expansion ◽  
Biologically Active ◽  
Valence Isomerization ◽  
Reduction Strategy ◽  
Quaternary Stereocenter

Disclosed is a four-step synthesis of (<i>±</i>)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one forges both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone furnishes a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. Our concise and modular route to the natural product provides the shortest total synthesis of (<i>±</i>)-vibralactone reported to date. <br>

ChemInform Abstract: Total Synthesis and Structural Revision of Mycalol, an Anticancer Natural Product from the Marine Source.

ChemInform ◽  
2015 ◽  
Vol 46 (34) ◽  
pp. no-no
Author(s):  
B. Seetharamsingh ◽  
P. R. Rajamohanan ◽  
D. Srinivasa Reddy
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Revision ◽  
Marine Source
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