An Enantioselective Synthesis of 1-Azaspiro[5.5]undecane Ring System of Histrionicotoxin Alkaloids from D(+)-Glucose

Heterocycles ◽  
2005 ◽  
Vol 65 (12) ◽  
pp. 2901 ◽  
Author(s):  
Smritilekha Bera
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis

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.

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

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

Enantioselective synthesis of the nagilactone ring system via vinylsilane-mediated polyene cyclization

1989 ◽  
Vol 30 (46) ◽  
pp. 6303-6306 ◽  
Author(s):  
Steven D. Burke ◽  
Sharon M.S. Strickland ◽  
Helen M. Organ ◽  
Louis A. Silks
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis

ChemInform Abstract: Biomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines.

ChemInform ◽  
2010 ◽  
Vol 41 (41) ◽  
pp. no-no
Author(s):  
Mercedes Amat ◽  
Robert Fabregat ◽  
Rosa Griera ◽  
Pedro Florindo ◽  
Elies Molins ◽  
...  
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis
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