Intramolecular Cyclization of Allylsilyl Substituted N-Acyliminium Ions. Access to 1- and 2-Azabicyclo[X.Y.0]alkanes. Total Synthesis of (±)-Mesembrine

Heterocycles ◽  
1992 ◽  
Vol 34 (1) ◽  
pp. 37 ◽  
Author(s):  
Roland Remuson ◽  
Yvonne Gelas-Mialhe ◽  
Jean-Claude Gramain ◽  
Hassane Hajouji ◽  
Roland Remuson
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Acyliminium Ions

scholarly journals Synthesis of macrocyclic terpenoids by intramolecular cyclization. XI. Total synthesis of zerumbone.

1987 ◽  
Vol 35 (10) ◽  
pp. 4039-4042 ◽  
Author(s):  
MITSUAKI KODAMA ◽  
YOSHINORI SHIOBARA ◽  
HISAKO SUMITOMO ◽  
KAZUKO MITANI ◽  
KUMIKO UENO
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization

Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

Studies on double acylation of aromatic hydrocarbons. XI. A total synthesis of 5,6-Dihydro-4H-benz[de]anthracene

1972 ◽  
Vol 25 (7) ◽  
pp. 1521 ◽  
Author(s):  
A Rahman ◽  
BM Vuano ◽  
NM Rodriguez
Keyword(s):  
Total Synthesis ◽  
Propionic Acid ◽  
Intramolecular Cyclization ◽  
Butyric Acid ◽  
Aromatic Hydrocarbons ◽  
Dibasic Acid ◽  
Membered Ring ◽  
Ring Closure ◽  
Partial Synthesis

Starting from ethyl 3-(1-naphthyl)propionate (1), the dibasic acid 4-(4-carboxy-ethyl-I-naphthyl)butyric acid (3) was prepared, which served as a key compound for the synthesis of 5,6-dihydro-4H-benz[de]anthraoene (6) by a double intramolecular cyclization. The monocyolization of the dibasic acid (3) gave rise by a preferential six-membered ring closure, to 3-(1-oxo-1,2,3,4-tetrahydro-9-phenanthryl)propionic acid (7). A partial synthesis of 5,6-dihydro-4H-benz[de]anthracene (6), by succinoylation of perinaphthane followed by usual synthetic steps, is reported as confirmatory evidence of the identity of (6) obtained by double cyclization of the diacid. Some aspects of the orientation of intramolecular acylation are discussed.

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone

Synlett ◽  
2017 ◽  
Vol 29 (04) ◽  
pp. 457-462 ◽  
Author(s):  
Mitsuru Kitamura ◽  
Dina Othman ◽  
Kota Otsuka ◽  
Shuhei Takahashi ◽  
Khalid Selim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Cyclization Reaction ◽  
Successful Strategy ◽  
Separation Of Diastereomers ◽  
Metal Catalyzed ◽  
Natural Cytotoxic

The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been ­accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-­catalyzed intramolecular cyclization reaction of the corresponding ­diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs–Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag2O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

Synthesis of macrocyclic terpenoids by intramolecular cyclization IX. Total synthesis of (±)-obscuronatin and (±)-biflora-4,10(19),15-triene.

1984 ◽  
Vol 25 (50) ◽  
pp. 5781-5784 ◽  
Author(s):  
Mitsuaki Kodama ◽  
Kunihito Okumura ◽  
Yoshihisa Kobayashi ◽  
Tetsuto Tsunoda ◽  
Shô Itô
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization

Total Synthesis of Bouchardatine

2013 ◽  
Vol 66 (9) ◽  
pp. 1112 ◽  
Author(s):  
Nilesh H. Naik ◽  
Tukaram D. Urmode ◽  
Arun K. Sikder ◽  
Radhika S. Kusurkar
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Type Reaction ◽  
Naturally Occurring

Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3-carbaldehyde (bouchardatine).

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