Reagent Control of [1,2]-Wagner-Meerwein Shift Chemoselectivity Following the Nazarov Cyclization: Application to the Total Synthesis of Enokipodin B

2013 ◽  
Vol 19 (15) ◽  
pp. 4835-4841 ◽  
Author(s):  
David Lebœuf ◽  
Christopher M. Wright ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
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

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.

Total Synthesis of (±)-Merrilactone A via Catalytic Nazarov Cyclization

2007 ◽  
Vol 129 (3) ◽  
pp. 498-499 ◽  
Author(s):  
Wei He ◽  
Jie Huang ◽  
Xiufeng Sun ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization ◽  
Merrilactone A
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