Regioselective and Stereoselective Heck–Matsuda Arylations of Trisubstituted Allylic Alkenols and Their Silyl and Methyl Ether Derivatives To Access Two Contiguous Stereogenic Centers: Expanding the Redox-Relay Process and Application in the Total Synthesis of meso-Hexestrol

2018 ◽  
Vol 83 (4) ◽  
pp. 2198-2209 ◽  
Author(s):  
Carlise Frota ◽  
Ellen Christine Polo ◽  
Henrique Esteves ◽  
Carlos Roque Duarte Correia
Keyword(s):  
Total Synthesis ◽  
Methyl Ether ◽  
Stereogenic Centers

Total synthesis of 14α-hydroxyestrone 3-methyl ether

1979 ◽  
pp. 2830-2835 ◽  
Author(s):  
Tetsuji Kametani ◽  
Hideo Nemoto ◽  
Masayoshi Tsubuki ◽  
Gediminas-Eugenijus Purvaneckas ◽  
Masahiro Aizawa ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Methyl Ether

Lignans. 13. Total Synthesis of (-)-Carinol, (-)-Carissanol and (-)-Hydroxythujaplicatin Methyl Ether

Heterocycles ◽  
1990 ◽  
Vol 31 (12) ◽  
pp. 2195 ◽  
Author(s):  
Eric Brown ◽  
Kenza Khamlach ◽  
Robert Dhal
Keyword(s):  
Total Synthesis ◽  
Methyl Ether

Enantioselective Organocatalytic Construction of Carbocycles: The Nicolaou Synthesis of Biyouyanagin A

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Methyl Ether ◽  
Conjugate Addition ◽  
Unsaturated Aldehyde ◽  
Enantiomerically Pure ◽  
Intramolecular Alkylation ◽  
Stereogenic Centers ◽  
Chinese Academy Of Sciences ◽  
Academy Of Sciences ◽  
Polycyclic System ◽  
Selective Addition

One of the more powerful routes to enantiomerically-pure carbocycles is the desymmetrization of a prochiral ring. Karl Anker Jørgensen of Aarhus University has found (J. Am. Chem. Soc. 2007, 129, 441) that many cyclic β-ketoesters, including the vinylogous carbonate 1, can be homologated with 2 to the corresponding alkyne 3, in high ee. Sanzhong Luo of the Chinese Academy of Sciences, Beijing, and Jin-Pei Cheng, of the Chinese Academy of Sciences and Nankai University, have shown (J. Org. Chem. 2007, 72, 9350) that the catalyst 6 mediated the selective addition of 4-substituted cyclohexanones such as 4 to the nitroalkene 5, establishing three new stereogenic centers. Organocatalysts, alone or complexed with activating metals, have also been used to effect enantioselective ring construction. E. J. Corey of Harvard University has established (J. Am. Chem. Soc. 2007, 129, 12686) that the proline-derived complex 10 will mediate the 2 + 2 addition of a cyclic enol ether with an acrylate to give the cyclobutane 11. Further elaboration led to the cyclohexenone 12. Armando Córdova of Stockholm University has described (Tetrahedron Lett. 2007, 48, 5835) a novel route to cyclopentanones such as 16, via tandem conjugate addition/intramolecular alkylation. Professor Jørgensen has reported (Angew. Chem. Int. Ed . 2007, 46 , 9202) the double addition of 18 to the unsaturated aldehyde 17 to give 20. Earlier last year, Yujiro Hayashi of the Tokyo University of Science had shown (Angew. Chem. Int. Ed. 2007, 46, 4922) that the double addition of the inexpensive 21 to 5 could, depending on conditions, be directed selectively to 22, 23, or 24. As illustrated by the conversion of 8 to 13, organocatalysis can be used to effect the enantioselective construction of polycarbocyclic products. The initial ring prepared in enantiomerically-pure form by organocatalysis can also set the chirality of a polycyclic system. Professor Corey has reported (J. Am. Chem. Soc. 2007, 129, 10346) that Itsuno-Corey reduction of the prochiral diketone 25 led to the ketone 27. Cyclization followed by oxidation and reduction then delivered estrone methyl ether 28.

Steroid total synthesis. X. Optically active estrone precursors and racemic equilenin methyl ether

1973 ◽  
Vol 38 (19) ◽  
pp. 3229-3239 ◽  
Author(s):  
Noal Cohen ◽  
Bruce L. Banner ◽  
John F. Blount ◽  
Moujau Tsai ◽  
Gabriel Saucy
Keyword(s):  
Total Synthesis ◽  
Methyl Ether ◽  
Optically Active
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