Total synthesis, stereochemistry, and lithium–ammonia reduction of (±)-4-demethylaristolone and (±)-5-epi-4-demethylaristolone

1969 ◽  
Vol 47 (23) ◽  
pp. 4299-4306 ◽  
Author(s):  
Edward Piers ◽  
William de Waal ◽  
Ronald W. Britton
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Similar Reduction ◽  
Dihydro Derivative

The total synthesis of (±)-4-demethylaristolone (14) and its epimer, (±)-5-epi-4-demethylaristolone (15) is described. The key step of this synthesis involves the intramolecular cyclization of the olefinic diazoketone 12, which produces the two epimers, 14 and 15, in a ratio of approximately 2:1, respectively. The stereochemistry of the two epimers is unambiguously determined. It is observed that the lithium–ammonia reduction of 14 gives a dihydro derivative 16 containing trans-fused six-membered rings, while, interestingly, a similar reduction of 15 affords the corresponding cis-fused decalone system 26.

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

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).

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

Total Synthesis ofepi-7-Deoxypancratistatin via Aza-Payne Rearrangement and Intramolecular Cyclization

2002 ◽  
Vol 4 (1) ◽  
pp. 115-117 ◽  
Author(s):  
Uwe Rinner ◽  
Peter Siengalewicz ◽  
Tomas Hudlicky
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization

Synthesis of macrocyclic terpenoids by intramolecular cyclization VII. Total synthesis of (±)-cubitene

1982 ◽  
Vol 23 (33) ◽  
pp. 3397-3400 ◽  
Author(s):  
Mitsuaki Kodama ◽  
Toshiya Takahashi ◽  
Tsutomu Kojima ◽  
Shô Itô
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization
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