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

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.

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.

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

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

scholarly journals Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

2019 ◽  
Vol 15 ◽  
pp. 2419-2427
Author(s):  
Sachin S Burade ◽  
Sushil V Pawar ◽  
Tanmoy Saha ◽  
Navanath Kumbhar ◽  
Amol S Kotmale ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Amino Acid ◽  
Molecular Modeling ◽  
Intramolecular Cyclization ◽  
Membered Ring ◽  
Conformational Study ◽  
Oxazole Ring ◽  
Solution State ◽  
Modeling Studies ◽  
Molecular Modeling Studies

The intramolecular cyclization of a C-3-tetrasubstituted furanoid sugar amino acid-derived linear tetrapeptide afforded an oxazolone pseudo-peptide with the formation of an oxazole ring at the C-terminus. A conformational study of the oxazolone pseudo-peptide showed intramolecular C=O···HN(II) hydrogen bonding in a seven-membered ring leading to a γ-turn conformation. This fact was supported by a solution-state NMR and molecular modeling studies. The oxazolone pseudotetrapeptide was found to be a better Cl−-selective transporter for which an anion–anion antiport mechanism was established.

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.

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