scholarly journals Total synthesis of dimeric Securinega alkaloids (−)-flueggenines D and I

2020 ◽  
Vol 11 (40) ◽  
pp. 10934-10938 ◽  
Author(s):  
Sangbin Jeon ◽  
Jinwoo Lee ◽  
Sangbin Park ◽  
Sunkyu Han
Keyword(s):  
Total Synthesis ◽  
Stille Reaction ◽  
Conjugate Reduction

The first total synthesis of dimeric securinega alkaloids (−)-flueggenines D and I was completed by a dimerization strategy that involves Stille reaction and stereoselective conjugate reduction.

scholarly journals Second Generation Synthesis of the Neo-Clerodane Diterpenoid Methyl Barbascoate

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Hisahiro Hagiwara ◽  
Naomi Honma ◽  
Kimihiko Kinugawa ◽  
Shota Sato ◽  
Takashi Hoshi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
Samarium Diiodide ◽  
Conjugate Reduction ◽  
Palladium Catalyzed ◽  
Clerodane Diterpenoid

The second generation total synthesis of the neo-clerodane diterpenoid, methyl barbascoate, was accomplished in seven or nine linear steps via double enol triflation and subsequent palladium catalyzed double carbonylation, followed by regioselective samarium diiodide mediated conjugate reduction.

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Total syntheses of smenothiazoles A and B

2017 ◽  
Vol 15 (34) ◽  
pp. 7196-7203 ◽  
Author(s):  
Xiao Ma ◽  
Yajie Chen ◽  
Sigui Chen ◽  
Zhengshuang Xu ◽  
Tao Ye
Keyword(s):  
Total Synthesis ◽  
Vinyl Chloride ◽  
Coupling Reactions ◽  
Stille Reaction ◽  
Total Syntheses ◽  
Peptide Coupling ◽  
Diene System

Stereocontrolled installation of vinyl chloride and the 2,5-diene system via silastannation, Stille reaction and desilylchlorination, and the final peptide coupling reactions led to the concise total synthesis of smenothiazoles A (1) and B (2).

scholarly journals Total Synthesis of 4-Acetyl-1,3-Dihydroimidazo[4,5-c]Pyridin-2-One, a New Microbial Metabolite from a Streptomyces Species

2009 ◽  
Vol 4 (7) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Tobias Bender ◽  
Paultheo von Zezschwitz
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Secondary Metabolite ◽  
Pyridine Derivative ◽  
Stille Reaction ◽  
Streptomyces Species ◽  
Streptomyces Sp ◽  
Microbial Metabolite

The structure of a new secondary metabolite from Streptomyces sp. was determined as 4-acetyl-1,3-dihydroimidazo[4,5-c]pyridin-2-one by synthesis of the natural product itself and of the regioisomeric 7-acetylimidazo[4,5-b]pyridine derivative. The former compound was prepared, in 28% overall yield, in a sequence of nitration, reduction, condensation, and Stille reaction of 4-aminopyridine, while the regioisomer was obtained in 5% overall yield by amination, nitration, reduction, condensation, and oxidation of 4-ethylpyridine.

Total synthesis of (–)-pateamine A, a novel immunosuppressive agent from Mycale sp

2004 ◽  
Vol 82 (2) ◽  
pp. 353-365 ◽  
Author(s):  
Gerald Pattenden ◽  
Douglas J Critcher ◽  
Modesto Remuiñán
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Sponge ◽  
Coupling Reaction ◽  
Immunosuppressive Agent ◽  
Side Chain ◽  
Amino Ester ◽  
Stille Reaction ◽  
Amino Esters ◽  
Pateamine A

A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (1) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp2–sp2 coupling reaction to elaborate the E,Z-diene macrolide core 23 and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters.

ChemInform Abstract: Recent Developments of the Stille Reaction as a Revolutionized Method in Total Synthesis

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
Majid M. Heravi ◽  
Elaheh Hashemi ◽  
Fereshteh Azimian
Keyword(s):  
Total Synthesis ◽  
Stille Reaction ◽  
Recent Developments
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