Concise Total Synthesis of (±)-Cephalotaxine via a Transannulation Strategy: Development of a Facile Reductive oxy-Nazarov Cyclization

2011 ◽  
Vol 13 (13) ◽  
pp. 3538-3541 ◽  
Author(s):  
Wei-Dong Z. Li ◽  
Wei-Guo Duo ◽  
Cheng-Han Zhuang
Keyword(s):  
Total Synthesis ◽  
Strategy Development ◽  
Nazarov Cyclization

scholarly journals Total Synthesis of (±)-Rocaglamide via Oxidation-Initiated Nazarov Cyclization

2012 ◽  
Vol 77 (4) ◽  
pp. 1891-1908 ◽  
Author(s):  
John A. Malona ◽  
Kevin Cariou ◽  
William T. Spencer ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization

scholarly journals Total Synthesis of (.+-.)-Merrilactone A via Catalytic Nazarov Cyclization.

ChemInform ◽  
2007 ◽  
Vol 38 (24) ◽  
Author(s):  
Wei He ◽  
Jie Huang ◽  
Xiufeng Sun ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization ◽  
Merrilactone A

scholarly journals Nazarov Cyclization Initiated by Peracid Oxidation: The Total Synthesis of (±)-Rocaglamide

2009 ◽  
Vol 131 (22) ◽  
pp. 7560-7561 ◽  
Author(s):  
John A. Malona ◽  
Kevin Cariou ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization

scholarly journals Total Synthesis of Nine Longiborneol Sesquiterpenoids Using a Functionalized Camphor Strategy

2021 ◽  
Author(s):  
Robert F. Lusi ◽  
Goh Sennari ◽  
Richmond Sarpong
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Strategy Development ◽  
Topological Complexity ◽  
Efficient Synthesis ◽  
Short Synthesis ◽  
Synthesis Routes ◽  
The 1960S

<p>Natural product total synthesis inspires strategy development in chemical synthesis. In the 1960s, Corey and coworkers demonstrated a visionary preparation of the terpenoid longifolene, using “strategic bond analysis” to craft a synthesis route. This approach proposes that efficient synthesis routes to bridged, polycyclic, structures should be formulated to introduce the bulk of the target’s topological complexity at a late stage. In subsequent decades, similar strategies have proved general for the syntheses of a wide variety of bridged, polycyclic molecules. Here, we demonstrate that an orthogonal strategy, which utilizes a topologically complex bicyclo[2.2.1] starting material accessed through a scaffold rearrangement of (<i>S</i>)-carvone, leads to a remarkably short synthesis of the longifolene-related terpenoid longiborneol. We also employ a variety of late-stage C–H functionalization tactics in divergent syntheses of many longiborneol congeners. Our strategy should prove effective for the preparation of other topologically complex natural products that contain the bicyclo[2.2.1] framework.</p>

Synthesis of C-Nor-D-homo-steroidal Alkaloids and Their Derivatives

Synthesis ◽  
2018 ◽  
Vol 50 (08) ◽  
pp. 1587-1600 ◽  
Author(s):  
Athanassios Giannis ◽  
Farnoush Mousavizadeh ◽  
Daniel Meyer
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Hedgehog Signaling ◽  
Nazarov Cyclization ◽  
Steroidal Alkaloids ◽  
Steroid Synthesis ◽  
Steroidal Alkaloid

The C-nor-D-homo-steroidal alkaloid cyclopamine was discovered in the 1969 and in 2000 it was shown to act as an inhibitor of the hedgehog signaling (Hh) pathway, which is aberrantly activated in some tumors. Subsequently it was revealed that this natural occurring alkaloid has also antidiabetic and antiviral properties. In this review we present syntheses of selected C-nor-D-homo-steroidal alkaloids and their analogues and also discuss a general access to C-nor-D-homo-steroids. Some historical as well as biomedical aspects are also presented.1 Introduction2 Total Synthesis of Cyclopamine2.1 Synthesis of exo-Cyclopamine and Further Cyclopamine Analogues2.2 Synthesis of a Carbacyclopamine Analogue3 D-Homocyclopamine: Saridegib (IPI-926)4 Synthesis of Nakiterpiosin5 Lewis Acid Mediated Nazarov Cyclization as a Versatile Method for C-Nor-D-homo-steroid Synthesis6 Conclusion

Stereocontrolled total synthesis of the triquinane marine sesquiterpene Δ9(12)-capnellene

1984 ◽  
Vol 62 (11) ◽  
pp. 2415-2420 ◽  
Author(s):  
Leo A. Paquette ◽  
Kenneth E. Stevens
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization ◽  
Marine Origin ◽  
Steric Factors ◽  
Chiral Centers

A total synthesis of Δ9(12)-capnellene, a cis-anti-cis-tricyclo[6.3.0.02,6]undecane sesquiterpene of marine origin, is described. Starting with bicyclic enone 5, which was prepared by a Nazarov cyclization, the remaining portion of the molecule is elaborated by means of a new and relatively efficient cyclopentenone annulation scheme. The relative stereochemistries of the chiral centers are properly incorporated by taking advantage of prevailing steric factors.

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