Diastereo- and Enantioselective Synthesis of a Novel Tetracyclic Ring System via an Organocatalytic One-Pot Reaction

2011 ◽  
Vol 353 (16) ◽  
pp. 2960-2965 ◽  
Author(s):  
De-Feng Yu ◽  
Yao Wang ◽  
Peng-Fei Xu
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
One Pot

scholarly journals Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 428
Author(s):  
Nihan Yayik ◽  
Maria Pérez ◽  
Elies Molins ◽  
Joan Bosch ◽  
Mercedes Amat
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Synthetic Route ◽  
Hydroxymethyl Group ◽  
Hydride Reduction ◽  
Lactam Carbonyl ◽  
Key Steps ◽  
Oxindole Alkaloids

A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3′-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the α-position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared.

An Efficient Organocatalysis: A One-Pot Highly Enantioselective Synthesis of α-Aminophosphonates

2013 ◽  
Vol 2013 (24) ◽  
pp. 5509-5516 ◽  
Author(s):  
Prashant B. Thorat ◽  
Santosh V. Goswami ◽  
Rupali L. Magar ◽  
Bhagwan R. Patil ◽  
Sudhakar R. Bhusare
Keyword(s):  
Enantioselective Synthesis ◽  
One Pot

Stereoselective One-Pot Method for the Introduction of an Amino Group to a Cyclohexane Ring. Preparation of the Octahydroisobenzofuro[7a,1-d]oxazole Ring System

Synthesis ◽  
1992 ◽  
Vol 1992 (12) ◽  
pp. 1261-1264 ◽  
Author(s):  
Kenji Saito ◽  
Hideo Takagi ◽  
Makoto Yamamoto ◽  
Kazutoshi Yamada
Keyword(s):  
Ring System ◽  
Cyclohexane Ring ◽  
Amino Group ◽  
One Pot ◽  
Oxazole Ring

Synthesis of Pyrazolofuropyrazine via One-Pot SNAr Reaction and Intramolecular Direct C–H Arylation

Synthesis ◽  
2018 ◽  
Vol 50 (07) ◽  
pp. 1493-1498 ◽  
Author(s):  
Shinichiro Fuse ◽  
Hiroyuki Nakamura ◽  
Megumi Inaba ◽  
Shinichi Sato ◽  
Manjusha Joshi
Keyword(s):  
Drug Discovery ◽  
Rapid Development ◽  
Ring System ◽  
Biologically Active ◽  
Drug Candidate ◽  
One Pot ◽  
Ring Systems ◽  
Drug Candidates ◽  
Fused Ring ◽  
Snar Reaction

Fused-ring systems containing heterocycles are attractive templates for drug discovery. Biologically active 6-5-5+6 fused-ring systems that possess heterocycles are available, but these require a relatively large number of synthetic steps for preparation. Therefore, pyrazolofuropyrazine was designed as a 6-5-5+6 ring system template that incorporates ready accessibility for drug discovery. Pyrazolofuropyrazines were successfully constructed in only a few steps via one-pot SNAr reaction/intramolecular C–H direct arylation. As a drug candidate, pyrazolofuropyrazine has earned a favorable LogP, although significant biological activity has yet to be established; the ready accessibility of pyrazolofuropyrazine template, however, offers an opportunity for the rapid development of promising new drug candidates.

A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

2001 ◽  
Vol 42 (18) ◽  
pp. 3235-3238 ◽  
Author(s):  
J.Stephen Clark ◽  
Robert J Townsend ◽  
Alexander J Blake ◽  
Simon J Teat ◽  
Amanda Johns
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Enyne Metathesis ◽  
Manzamine Alkaloids ◽  
Ab Ring

scholarly journals One-pot synthesis of (R)-convolutamydine A involving in situ chiral organocatalyst formation

2015 ◽  
Vol 2 (1) ◽  
Author(s):  
Shengwei Wei ◽  
Bernhard Schmid ◽  
Fliur Z. Macaev ◽  
Serghei N. Curlat ◽  
Andrei V. Malkov ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
One Pot ◽  
One Pot Synthesis ◽  
Synthetic Strategy

Abstract The application of a convenient one-pot synthetic strategy, utilizing an in situ formed organocatalyst, to the enantioselective synthesis of anti-leukaemia agent (R)-convolutamydine A has been demonstrated.

A New Access to the 6,8-Dioxabicyclo[3.2.1]octane Ring System Using a Three-Component Reaction: Enantioselective Synthesis of (+)-iso-exo-Brevicomin

Synlett ◽  
2009 ◽  
Vol 2010 (02) ◽  
pp. 207-210 ◽  
Author(s):  
François Carreaux ◽  
Asmae Bouziane ◽  
Thomas Régnier ◽  
Bertrand Carboni ◽  
Christian Bruneau ◽  
...  
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Three Component Reaction
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