ChemInform Abstract: Installation of the Pyruvate Unit in Glycidic Aldehydes via a Wittig Olefination-Michael Addition Sequence Utilizing a Thiazole-Armed Carbonyl Ylid. A New Stereoselective Route to 3-Deoxy-2-Ulosonic Acids and the Total Synthesis of DA

ChemInform ◽  
2010 ◽  
Vol 25 (34) ◽  
pp. no-no
Author(s):  
A. DONDONI ◽  
A. MARRA ◽  
P. MERINO
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Wittig Olefination

scholarly journals Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3224
Author(s):  
Leander Geske ◽  
Ulrich Kauhl ◽  
Mohamed E. M. Saeed ◽  
Anja Schüffler ◽  
Eckhard Thines ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Total Syntheses ◽  
Wittig Olefination ◽  
Starting Point ◽  
Perkin Reaction ◽  
Synthesis And Biological Evaluation

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

scholarly journals Towards the total synthesis of keramaphidin B

2016 ◽  
Vol 12 ◽  
pp. 1096-1100 ◽  
Author(s):  
Pavol Jakubec ◽  
Alistair J M Farley ◽  
Darren J Dixon
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Synthetic Strategy

The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.

Synthesis of 14-hydroxy steroids. Total synthesis of methyl 14β-hydroxy-1,7,17-trioxo-5β,8-androstene-10β-oate and related compounds

1990 ◽  
Vol 68 (11) ◽  
pp. 1917-1922 ◽  
Author(s):  
Réjean Ruel ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Michael Addition ◽  
Title Compound ◽  
Steroid Synthesis ◽  
Related Compounds ◽  
Acetylenic Ketone

The total synthesis of the title compound 22 and methyl 14α-hydroxy-5β,13α,8-androstene-1,7,17-trioxo-10β-oate 21 isomer is reported. We also describe the 1,6-Michael addition of 2-methyl-1,3-cyclopentanedione on dienone 14 and the protic ammonium salt catalyzed intramolecular Michael addition of cyclic β-ketoester on the conjugated acetylenic ketone 13. Keywords: cardenolides, steroid synthesis, aldol, Michael addition.

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

Intramolecular Michael Addition of N- and O-Centred Nucleophiles to Tethered Acrylates. The Role of Double-Bond Geometry in Controlling the Diastereo- selectivity of Cyclizations Leading to 2,6-Disubstituted Tetrahydropyrans and Piperidines.

1998 ◽  
Vol 51 (1) ◽  
pp. 9 ◽  
Author(s):  
Martin G. Banwell ◽  
Brett D. Bissett ◽  
Chinh T. Bui ◽  
Ha T. T. Pham ◽  
Gregory W. Simpson
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Michael Addition ◽  
Reductive Amination ◽  
Major Product ◽  
Enantioselective Synthesis ◽  
Cyclization Reactions ◽  
Glandular Secretion

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

The Total Synthesis of Spermine Alkaloid Kukoamine Bimesylate

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2669-2672
Author(s):  
Kai Dong
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Cyano Group ◽  
Michael Addition Reaction ◽  
Amino Groups ◽  
Competitive Reaction ◽  
12 Steps ◽  
Cyano Groups

The first total synthesis of kukoamine B bimesylate was completed from 1,4-diaminobutane dihydrochloride in 12 steps with a 11.4% overall yield, and all the steps could be carried out at a kilogram scale. The cyano groups were used as the precursor of amino groups to avoid the competitive reaction delicately. The aza-Michael addition reaction, amidation and hydrogenation of the cyano group sequence was streamlined as a general approach towards the synthesis of polyamine structures.

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