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 indole and dihydroindole alkaloids. II. Partial synthesis of some nine-membered ring intermediates from catharanthine

1970 ◽  
Vol 92 (6) ◽  
pp. 1704-1707 ◽  
Author(s):  
James P. Kutney ◽  
Walter J. Cretney ◽  
John R. Hadfield ◽  
Ernest Stanley. Hall ◽  
Vern R. Nelson
Keyword(s):  
Total Synthesis ◽  
Membered Ring ◽  
Partial Synthesis

Formal total synthesis of salvianolic acid N

2018 ◽  
Vol 16 (5) ◽  
pp. 832-837 ◽  
Author(s):  
Kong Wu ◽  
Zhong Pao Xie ◽  
Dong-Mei Cui ◽  
Chen Zhang
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Wittig Reaction ◽  
Membered Ring ◽  
Salvianolic Acid

Salvianolic acid N was synthesized starting from 3,4-dimethoxybenzaldehyde in 11 steps and with an overall yield of 11%. The key reaction steps were the Wittig reaction for Z-stereoselectivity, the copper catalyzed intramolecular cyclization for seven membered ring skeleton, and the deprotected allylic group with Pd catalysis.

The Chemistry of Pyrrolic Compounds. LXIV. Intramolecular Cyclization of Butyric Acid Substituted Porphyrins: Petroporphyrins With Fused Seven-Membered Ring Systems

1990 ◽  
Vol 43 (5) ◽  
pp. 839 ◽  
Author(s):  
PS Clezy ◽  
U Jenie ◽  
JK Prashar
Keyword(s):  
Intramolecular Cyclization ◽  
Butyric Acid ◽  
Membered Ring ◽  
Side Chains ◽  
Ring Systems ◽  
Porphyrin Macrocycle

The preparation of a series of porphyrins substituted with butyric acid side chains is described and efforts to achieve the intramolecular cyclization of this substituent are discussed. Attempts to prepare a stable spiro ketone by cyclization onto a β- pyrrolic carbon have not met with success but the synthesis of a seven- membered ring ketone by cyclization onto a meso -carbon has been completed. Reduction of this ketone has led to the synthesis of the petroporphyrin (1d). Some comments are offered concerning the origin of the isomeric petroporphyrin (19a) which bears a methylated six- membered ring sytem fused to the porphyrin macrocycle.

Synthesis of macrocyclic terpenoids by intramolecular cyclization. 12. Total synthesis of methyl ceriferate I, a 14-membered ring sesterterpene from scale insects

1988 ◽  
Vol 53 (7) ◽  
pp. 1437-1441 ◽  
Author(s):  
Mitsuaki Kodama ◽  
Yoshinori Shiobara ◽  
Hisako Sumitomo ◽  
Kazuyoshi Fukuzumi ◽  
Hiroyuki Minami ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Membered Ring ◽  
Scale Insects

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

On terpenes. LVIII. Total synthesis of 1,1,4,8-tetramethylcycloundecane: Proof of the eleven-membered ring in humulene

1954 ◽  
Vol 19 (3) ◽  
pp. 570-580 ◽  
Author(s):  
F. Šorm ◽  
M. Streibl ◽  
V. Jarolím ◽  
L. Novotný ◽  
L. Dolejš ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Membered Ring

XXI.—The Synthesis of Some Methyl- and Dimethylfluoranthenes

1972 ◽  
Vol 69 (4) ◽  
pp. 281-286
Author(s):  
H. F. Andrew ◽  
Neil Campbell ◽  
E. M. Swan ◽  
N. H. Wilson
Keyword(s):  
Benzene Ring ◽  
Propionic Acid ◽  
Hydrofluoric Acid ◽  
Phenyl Ring ◽  
Ring Closure ◽  
Methyl Group ◽  
Image Position

3-Methylfluorene-9-propionic acid (1) with hydrofluoric acid undergoes ring-closure on the substituted ring to give 1,2,3,10b-tetrahydro-5-methylfluoranthen-3-one (II).Wolff-Kishner reduction of the ketone yielded l,2,3,10b-tetrahydro-5-methylfluoranthene which on dehydrogenation gave 2-methylfluoranthene (III, R=H) identical with a sample prepared according to the method of Tucker (1952) and differing from 8-methylfluoranthene. This proved that ring-closure of (I) had occurred as expected on the methyl-bearing benzene ring. In this instance ring-closure occurs in the position meta to the methyl group and is reminiscent of the similar ring-closure of 2-phenyl-2-p-tolylpropionic acid to give 6-methyl-3-phenylindanone (Pfeiffer and Roos 1941). It thus provided a further example of the limitations of von Braun's statement that Friedel-Crafts ring-closure occurs much less readily at the position meta to a methyl group than on a phenyl ring (von Braun, Manz and Reinsch 1928).

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