Total synthesis of (±)-aristolone

1969 ◽  
Vol 47 (5) ◽  
pp. 831-840 ◽  
Author(s):  
Edward Piers ◽  
Ronald W. Britton ◽  
William de Waal
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Cupric Sulfate ◽  
Racemic Form

A novel and efficient total synthesis of the racemic form of the sesquiterpene (−)-aristolone (1) is presented. The key step involves the cupric sulfate catalyzed intramolecular cyclization of the diazoketone 27, which produces a mixture of products, the major component of which is (±)-aristolone.

Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

1971 ◽  
Vol 49 (1) ◽  
pp. 12-19 ◽  
Author(s):  
Edward Piers ◽  
Ronald W. Britton ◽  
William De Waal
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
High Yield ◽  
Cupric Sulfate ◽  
The Novel

An efficient total synthesis of the racemic forms of the novel tricyclic sesquiterpenes α-cubebene (1) and β-cubebene (2) is described. The key step of this synthesis involved the cupric sulfate catalyzed intramolecular cyclization of the olefinic diazoketone 3, which produced, in high yield, ( ± )-β-cubebene norketone (24) and ( ± )-1,6-epi-β-cubebene norketone (25), in a ratio of approximately 3:5, respectively.

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

An intermolecular Diels–Alder approach to (±)-isoacanthodoral

1994 ◽  
Vol 72 (12) ◽  
pp. 2416-2427 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Gerardo Ulibarri ◽  
Lloyd A. K. Nelson
Keyword(s):  
Total Synthesis ◽  
Boron Trifluoride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Racemic Form ◽  
Diels Alder Reaction

The total synthesis of marine sesquiterpenoid isoacanthodoral (3), in racemic form, has been accomplished, using the boron trifluoride catalyzed Diels–Alder reaction of dienone ester 4 and isoprene as the key step.

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).

Thermal rearrangement of functionalized 6-exo-(1-alkenyl)bicyclo[3.1.0]hex-2-enes. A total synthesis of (±)-sinularene

1985 ◽  
Vol 63 (4) ◽  
pp. 996-998 ◽  
Author(s):  
Edward Piers ◽  
Grace L. Jung
Keyword(s):  
Total Synthesis ◽  
Thermal Rearrangement ◽  
Racemic Form

A total synthesis of the racemic form of the marine sesquiterpenoid (−)-sinularene (1) is described. The key step of the synthesis involved the stereoselective thermal rearrangement of the highly functionalized bicyclo[3.1.0]hexene 12 to provide, in 86% yield, the substituted bicyclo[3.2.1]octadiene 13. Conversion of the latter substance into (±)-sinularene (1) was accomplished via an efficient 4-step sequence.

Annulation via donor-acceptor reagents. An efficient total synthesis of (±)-∆9(12)-capnellene

1984 ◽  
Vol 62 (3) ◽  
pp. 629-631 ◽  
Author(s):  
E. Piers ◽  
V. Karunaratne
Keyword(s):  
Total Synthesis ◽  
Grignard Reagent ◽  
Conjugate Addition ◽  
Intramolecular Alkylation ◽  
Racemic Form ◽  
Donor Acceptor ◽  
Key Steps

A short, efficient total synthesis of the racemic form of the marine sesquiterpenoid (-)-∆9(12)-capnellene (1) is described. The key steps of the synthesis are two methylenecyclopentane annulation sequences (14 → 16; 22 → 24) involving the CuBr-Me2S→BF3 • Et2O catalyzed conjugate addition of the Grignard reagent 13 to the enones 14 and 22, followed by intramolecular alkylation (KH, tetrahydrofuran) of the resultant adducts 15 and 23, respectively

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