Total synthesis of (−)-20-epiuleinevia stereocontrolled one-pot asymmetric azaelectrocyclization followed by novel 1,4-addition reaction

2011 ◽  
Vol 9 (1) ◽  
pp. 257-264 ◽  
Author(s):  
Taku Sakaguchi ◽  
Shohei Kobayashi ◽  
Shigeo Katsumura
Keyword(s):  
Total Synthesis ◽  
Addition Reaction ◽  
One Pot

Concise total synthesis of (±)-aspidospermidine

2015 ◽  
Vol 13 (18) ◽  
pp. 5255-5259 ◽  
Author(s):  
Haichen Ma ◽  
Xingang Xie ◽  
Peng Jing ◽  
Weiwei Zhang ◽  
Xuegong She
Keyword(s):  
Total Synthesis ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
One Pot ◽  
Carbonyl Reduction

(±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the synthesis of other kinds of Aspidosperma alkaloids.

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy

2013 ◽  
Vol 54 (6) ◽  
pp. 506-511 ◽  
Author(s):  
Hiromi Uchiro ◽  
Nobuhiro Shionozaki ◽  
Ryo Tanaka ◽  
Hiroyuki Kitano ◽  
Naoki Iwamura ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cascade Reaction ◽  
One Pot

Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies

2006 ◽  
Vol 84 (10) ◽  
pp. 1226-1241 ◽  
Author(s):  
Peter Wipf ◽  
Michel Grenon
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Recent Progress ◽  
Furan Ring ◽  
Addition Reaction ◽  
Thermal Conditions ◽  
Preliminary Results ◽  
Keto Esters ◽  
New Methodologies ◽  
Metal Catalyzed

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.

ChemInform Abstract: A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (.+-.)-Laurokamurene B.

ChemInform ◽  
2010 ◽  
Vol 41 (9) ◽  
Author(s):  
Jean Tallineau ◽  
Georges Bashiardes ◽  
Jean-Marie Coustard ◽  
Frederic Lecornue
Keyword(s):  
Total Synthesis ◽  
One Pot

A Concise Total Synthesis of (±)-Mesembrine

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1203-1206 ◽  
Author(s):  
Hyoungsu Kim ◽  
Hosam Choi ◽  
Kiyoun Lee
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Allylic Oxidation ◽  
Quaternary Stereocenter

A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson–Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.

A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (±)-Laurokamurene B

Synlett ◽  
2009 ◽  
Vol 2009 (17) ◽  
pp. 2761-2764 ◽  
Author(s):  
Frédéric Lecornué ◽  
Jean Tallineau ◽  
Georges Bashiardes ◽  
Jean-Marie Coustard
Keyword(s):  
Total Synthesis ◽  
One Pot
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