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>

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>

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: Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis.

ChemInform ◽  
2010 ◽  
Vol 41 (27) ◽  
pp. no-no
Author(s):  
Matthew Brichacek ◽  
Lindsay A. Batory ◽  
Jon T. Njardarson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Ring Expansion

scholarly journals Synthesis of Highly Functionalised Furo[3,4-b]pyrans: Towards the Fungal Metabolite (−)-TAN-2483B

2021 ◽  
Author(s):  
◽  
R.M. Kalpani K. Somarathne
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Cyclopropane Ring ◽  
Ring Expansion ◽  
Ethyl Esters ◽  
Pyran Ring ◽  
Synthetic Strategy ◽  
Alternative Approach ◽  
Synthetic Approaches

<p>Carbohydrate-derived cyclopropanes combine both the stereochemical wealth of carbohydrates and the reactivity of cyclopropanes. A diverse variety of reaction modes for these cyclopropyl carbohydrates can be harnessed for the synthesis of natural products and other targets.  The natural products (−)-TAN-2483A and (−)-TAN-2483B are fungal secondary metabolites displaying a variety of bioactivities such as inhibition of c-src kinase action and parathyroid hormone-induced bone resorption. This thesis described several synthetic approaches to the natural product (−)-TAN-2483B and analogues of (−)-TAN-2483B employing cyclopropane ring expansion.  The synthetic route to (−)-TAN-2483B began with the readily available substrate D-mannose. The pyran ring unsaturation of the natural product was established by a cyclopropanation-ring expansion sequence. A synthetic strategy via dichlorocyclopropane-based intermediates is described in chapter 2. This being unsuccessful, an alternative approach via 2-fomyl-glycal was developed in chapter 3. The chapter 2 and 3 provided a solid background for the achievement of the analogues synthesis illustrated in chapter 4 via dibromocyclopropane. Lewis acid-mediated alkynylation followed by Pdcatalysed carbonylative lactonisation was successfully utilised in the revelation of the furo[3,4-b]pyran ring skeleton. This route afforded analogues of TAN-2483B; the Z-and E-unsaturated ethyl esters 140 and 141 and hydroxy(−)-TAN-2483B 145. The total synthesis of (−)-TAN-2483B was not achieved due to unforeseen obstacles encountered in the deoxygenation of the side arm of 335 (Chapter 4) into the E-propenyl side arm of (−)-TAN-2483B.</p>

Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis

2010 ◽  
Vol 49 (9) ◽  
pp. 1648-1651 ◽  
Author(s):  
Matthew Brichacek ◽  
Lindsay A. Batory ◽  
Jon T. Njardarson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Ring Expansion

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.

Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis

2010 ◽  
Vol 122 (9) ◽  
pp. 1692-1695 ◽  
Author(s):  
Matthew Brichacek ◽  
Lindsay A. Batory ◽  
Jon T. Njardarson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Ring Expansion

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.

Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2878-2886 ◽  
Author(s):  
Fernando Sartillo-Piscil ◽  
Julio Romero-Ibañez ◽  
Silvano Cruz-Gregorio ◽  
Leticia Quintero
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation Reaction ◽  
Optical Rotation ◽  
Environmentally Friendly ◽  
Biologically Active ◽  
Synthetic Material ◽  
Asymmetric Total Synthesis ◽  
Nmr Data ◽  
Environmentally Friendly Approach

An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.

scholarly journals Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12626-12652 ◽  
Author(s):  
Amardeep Awasthi ◽  
Mandeep Singh ◽  
Garima Rathee ◽  
Ramesh Chandra
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Contextual Information ◽  
Natural Product Synthesis ◽  
Biologically Active ◽  
Synthetic Methodologies ◽  
Active Natural

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