Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1547-1556 ◽  
Author(s):  
Christiana Teijaro ◽  
Senzhi Zhao ◽  
Praveen Kokkonda ◽  
Rodrigo Andrade
Keyword(s):  
Heck Reaction ◽  
Second Generation ◽  
One Pot ◽  
Total Syntheses ◽  
Tetracyclic Core ◽  
Key Steps ◽  
First And Second Generation ◽  
Intramolecular Heck Reaction

The first enantioselective total syntheses of (–)-alstolucinces A, B, and F, (–)-echitamidine, and (–)-N-demethylalstogucine are reported. This article details the development of our first- and second-generation approaches toward the ABCE tetracyclic core of the strychnos alkaloids and the application thereof to the aforementioned targets. Key steps involve our sequential one-pot biscyclization method that constructs the C and E rings of the tetracyclic core and Rawal’s application of the intramolecular Heck reaction to secure the pentacyclic framework common amongst all targets.

Novel Total Syntheses of (.+-.)-Oxerine by Intramolecular Heck Reaction.

ChemInform ◽  
2004 ◽  
Vol 35 (10) ◽  
Author(s):  
Jingrui Zhao ◽  
Xiaoxia Yang ◽  
Xueshun Jia ◽  
Shengjun Luo ◽  
Hongbin Zhai
Keyword(s):  
Heck Reaction ◽  
Total Syntheses ◽  
Intramolecular Heck Reaction

Intramolecular Heck reaction: A facile sequential one-pot synthesis of 1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines

2018 ◽  
Vol 59 (45) ◽  
pp. 4039-4043 ◽  
Author(s):  
Puchakayala Bharath Kumar Reddy ◽  
Kanakaraju Ravi ◽  
Kukkamudi Mahesh ◽  
Panaganti Leelavathi
Keyword(s):  
Heck Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Intramolecular Heck Reaction

Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol and (±)-amijitrienol

1992 ◽  
Vol 70 (4) ◽  
pp. 1204-1220 ◽  
Author(s):  
Edward Piers ◽  
Richard W. Friesen
Keyword(s):  
Aldol Condensation ◽  
Ring Closure ◽  
Starting Material ◽  
Target Compound ◽  
One Pot ◽  
Stereoselective Reduction ◽  
Total Syntheses ◽  
Reductive Transformation ◽  
The One ◽  
Key Steps

Alkylation of the substituted cycloalkanones 14a–d and 30 with (Z)-1-bromo-4-methyl-3-trimethylstannyl-2-pentene (13) produced compounds 15a–d and 33, which were readily converted into the corresponding enol trifluoromethane-sulfonates (triflates) 16a–d and 34. Intramolecular Pd(O)-catalyzed coupling of the vinylstannane and enol triflate functions in 16a–d and 34 provided the dienes 17a–d and 35. The annulation product 35 served as a suitable starting material for the total syntheses of the dolastane diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol (2) and (±)-amijitrienol (3). The key steps of the synthesis of (±)-2 involved the stereoselective methylation of the ketone 44 (readily derived from 35) to provide 46 and the Barbier type ring closure of 47 to provide the target compound. For the synthesis of (±)-3, the notable conversions included the reductive transformation of the diene 35 into the alkene 53, the aldol condensation of the ketone 54 with 4-trimethylstannyl-4-pentenal (55), the chemo- and stereoselective reduction of the dione 58, and the one-pot conversion of the keto vinylstannane 63 into the triene 65, via the intermediate 64.

ChemInform Abstract: Facile Construction of Pyrrolophenanthridone Skeleton via a One-Pot Intramolecular Heck Reaction and Oxidation.

ChemInform ◽  
2014 ◽  
Vol 45 (27) ◽  
pp. no-no
Author(s):  
Wei Cong ◽  
Lei Zhao ◽  
Xiaoming Wu ◽  
Jinyi Xu ◽  
Hequan Yao
Keyword(s):  
Heck Reaction ◽  
One Pot ◽  
Intramolecular Heck Reaction

Facile construction of pyrrolophenanthridone skeleton via a one-pot intramolecular Heck reaction and oxidation

Tetrahedron ◽  
2014 ◽  
Vol 70 (2) ◽  
pp. 312-317 ◽  
Author(s):  
Wei Cong ◽  
Lei Zhao ◽  
Xiaoming Wu ◽  
Jinyi Xu ◽  
Hequan Yao
Keyword(s):  
Heck Reaction ◽  
One Pot ◽  
Intramolecular Heck Reaction

Novel total syntheses of (±)-oxerine by intramolecular Heck reaction

Tetrahedron ◽  
2003 ◽  
Vol 59 (47) ◽  
pp. 9379-9382 ◽  
Author(s):  
Jingrui Zhao ◽  
Xiaoxia Yang ◽  
Xueshun Jia ◽  
Shengjun Luo ◽  
Hongbin Zhai
Keyword(s):  
Heck Reaction ◽  
Total Syntheses ◽  
Intramolecular Heck Reaction

Organocatalytic total synthesis of bioactive compounds based on one-pot methodologies

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Hélène Pellissier
Keyword(s):  
Total Synthesis ◽  
Bioactive Compounds ◽  
Biologically Active ◽  
Direct Access ◽  
Tandem Reactions ◽  
One Pot ◽  
Total Syntheses ◽  
Asymmetric Organocatalysis ◽  
Key Steps

Abstract The combination of one-pot methodologies to asymmetric organocatalysis allow a green and direct access to many types of complex highly functionalized chiral products, including important key intermediates in total syntheses of important bioactive compounds. A series of chiral organocatalysts have already been successfully applied to such syntheses. This report collects major developments in the total synthesis of biologically active products based on the use of enantioselective organocatalytic domino/tandem reactions as key steps. It is divided into two parts dealing successively with reactions based on the use of proline-derived catalysts and other organocatalysts.

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