Enantioselective Synthesis of the AB-Ring System of the Antitumor Antibiotic Tetrazomine

2001 ◽  
Vol 66 (9) ◽  
pp. 3133-3139 ◽  
Author(s):  
Peter Wipf ◽  
Corey R. Hopkins
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Antitumor Antibiotic ◽  
Ab Ring

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 Enantioselective Synthesis of the Predominant AB Ring System of the Schisandra Nortriterpenoid Natural Products

2014 ◽  
Vol 16 (17) ◽  
pp. 4480-4483 ◽  
Author(s):  
Birgit Gockel ◽  
Shermin S. Goh ◽  
Emma J. Puttock ◽  
Hannah Baars ◽  
Guilhem Chaubet ◽  
...  
Keyword(s):  
Natural Products ◽  
Ring System ◽  
Enantioselective Synthesis ◽  
Ab Ring

ChemInform Abstract: A Concise Enantioselective Synthesis of the AB Ring System of the Manzamine Alkaloids by Ring-Closing Enyne Metathesis.

ChemInform ◽  
2010 ◽  
Vol 32 (29) ◽  
pp. no-no
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 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.

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