Total Synthesis of (−)-(α)-Kainic Acid via a Diastereoselective Intramolecular [3 + 2] Cycloaddition Reaction of an Aryl Cyclopropyl Ketone with an Alkyne

2012 ◽  
Vol 14 (10) ◽  
pp. 2540-2543 ◽  
Author(s):  
Zhi Luo ◽  
Bing Zhou ◽  
Yuanchao Li
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Cycloaddition Reaction ◽  
Cyclopropyl Ketone

Asymmetric, stereocontrolled total synthesis of (+) and (−)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

Tetrahedron ◽  
2002 ◽  
Vol 58 (32) ◽  
pp. 6311-6322 ◽  
Author(s):  
Paul R Sebahar ◽  
Hiroyuki Osada ◽  
Takeo Usui ◽  
Robert M Williams
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

Total synthesis of barbatane sesquiterpenes: α- and β-barbatenes, gymnomitrol, and isogymnomitrol

1979 ◽  
Vol 57 (24) ◽  
pp. 3343-3345 ◽  
Author(s):  
Mitsuaki Kodama ◽  
Toshio Kurihara ◽  
Jinko Sasaki ◽  
Shô Itô
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Skeletal Rearrangements

A total synthesis of the barbatenes and a formal total synthesis of gymnomitrol and isogymnomitrol were achieved through a common intermediate utilizing a cycloaddition reaction and skeletal rearrangements.

An enantiospecific total synthesis of (–)-α-kainic acid

1987 ◽  
pp. 1220-1222 ◽  
Author(s):  
Jeremy Cooper ◽  
David W. Knight ◽  
Peter T. Gallagher
Keyword(s):  
Total Synthesis ◽  
Kainic Acid

Synthetic Studies towards the Total Synthesis of Indole Alkaloids Containing Indolyl Lactam Frameworks

Synlett ◽  
2020 ◽  
Author(s):  
Fu-She Han ◽  
Dong-Xing Tan
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Cycloaddition Reaction ◽  
Terminal Olefin ◽  
Asymmetric Reaction ◽  
Rapid Construction ◽  
Fused Ring ◽  
Acid Catalyzed ◽  
Synthetic Studies ◽  
Type Substitution

AbstractIn this account, recent progress on the synthetic studies of several monoterpene indole alkaloids, (±)-mersicarpine, misassigned (±)-tronoharine, and (±)-leuconodines D and E, is summarized. Specifically, the rationale for the design and development of the Lewis acid catalyzed SN1-type substitution and formal [3+3] cycloaddition reaction of indol-2-yl carbinols, and the Pd-catalyzed aerobic oxidative intramolecular Heck cross-coupling of indolyl amides tethered with a terminal olefin functionality, are emphasized. These key reactions set the basis for the rapid construction of the fused ring skeleton containing an all-carbon quaternary center at the indol-2-yl position.1 Introduction2 Synthetic Study of (±)-Mersicarpine3 Synthetic Study of the Misassigned (±)-Tronoharine4 Study of the Asymmetric Reaction of Indol-2-yl Carbinols5 Synthetic Study of (±)-Leuconodines D and E6 Conclusion

Total Synthesis of (−)-Kainic Acid via Intramolecular Michael Addition: A Second-Generation Route

2008 ◽  
Vol 10 (9) ◽  
pp. 1711-1714 ◽  
Author(s):  
Hiroshi Sakaguchi ◽  
Hidetoshi Tokuyama ◽  
Tohru Fukuyama
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Michael Addition ◽  
Second Generation

A total synthesis of (-)-α-kainic acid by the Pauson-Khand reaction

1993 ◽  
Vol 34 (21) ◽  
pp. 3435-3438 ◽  
Author(s):  
Yoo Sung-eun ◽  
Lee Sang-Hee ◽  
Jeong Nakcheol ◽  
Cho Inho
Keyword(s):  
Total Synthesis ◽  
Kainic Acid

Ruthenium-Catalyzed Alkyne−Propargyl Alcohol Addition. An Asymmetric Total Synthesis of (+)-α-Kainic Acid

2003 ◽  
Vol 5 (9) ◽  
pp. 1467-1470 ◽  
Author(s):  
Barry M. Trost ◽  
Michael T. Rudd
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Propargyl Alcohol ◽  
Asymmetric Total Synthesis

Total Synthesis of (±)-Kainic Acid with an Aza-[2,3]-Wittig Sigmatropic Rearrangement as the Key Stereochemical Determining Step

2003 ◽  
Vol 68 (16) ◽  
pp. 6160-6163 ◽  
Author(s):  
James C. Anderson ◽  
Matthew Whiting
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Sigmatropic Rearrangement
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