scholarly journals Total Synthesis and Structural Reassignment of Laingolide A

Marine Drugs ◽  
2021 ◽  
Vol 19 (5) ◽  
pp. 247
Author(s):  
Fusong Wu ◽  
Tao Zhang ◽  
Jie Yu ◽  
Yian Guo ◽  
Tao Ye
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Total Synthesis ◽  
Type Coupling ◽  
Salient Features ◽  
Unambiguous Assignment

The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.

Asymmetric total synthesis of naturally occurring spirocyclic tetranorsesquiterpenoid lanceolactone A

2018 ◽  
Vol 16 (27) ◽  
pp. 5027-5035 ◽  
Author(s):  
Ranjan Kumar Acharyya ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Total Synthesis ◽  
Cascade Cyclization ◽  
Naturally Occurring

Asymmetric total synthesis of naturally occurring γ-butenolide containing [4.4]spiro-tetrahydrofuran lanceolactone A has been reported in this present work. Bimetallic (“Pd–Cu”) cascade cyclization was the crucial reaction employed for the construction of the γ-butenolide framework of the natural product.

Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus

2018 ◽  
Vol 16 (27) ◽  
pp. 5043-5049 ◽  
Author(s):  
Yi Man ◽  
Shaomin Fu ◽  
Juan Chen ◽  
Bo Liu
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Total Synthesis ◽  
Structural Revision

Asymmetric total synthesis of compound 1, as a proposed molecular structure of a natural product, in 11 steps is described. The inconsistency of the characterization data prompted us to propose a different structure as compound 2 and accordingly accomplish total synthesis in 9 steps and confirm the structural revision of this natural product.

Asymmetric Total Synthesis of Pentacyclic Indole Alkaloid Andranginine and Absolute Configuration of Natural Product Isolated from Kopsia arborea

2017 ◽  
Vol 19 (10) ◽  
pp. 2722-2725 ◽  
Author(s):  
Shino Tooriyama ◽  
Yuji Mimori ◽  
Yuqiu Wu ◽  
Noriyuki Kogure ◽  
Mariko Kitajima ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Absolute Configuration ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis

The Cyclodehydration Route to the Asymmetric Total Synthesis of the Marine Natural Product Isolated from the Brown Alga,Notheia Anomala

1993 ◽  
Vol 22 (3) ◽  
pp. 477-480 ◽  
Author(s):  
Hidenori Chikashita ◽  
Yusuke Nakamura ◽  
Hiromitsu Uemura ◽  
Kazuyoshi Itoh
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Brown Alga ◽  
Marine Natural Product ◽  
Asymmetric Total Synthesis

Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2878-2886 ◽  
Author(s):  
Fernando Sartillo-Piscil ◽  
Julio Romero-Ibañez ◽  
Silvano Cruz-Gregorio ◽  
Leticia Quintero
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation Reaction ◽  
Optical Rotation ◽  
Environmentally Friendly ◽  
Biologically Active ◽  
Synthetic Material ◽  
Asymmetric Total Synthesis ◽  
Nmr Data ◽  
Environmentally Friendly Approach

An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.

The first asymmetric total synthesis of lycoposerramine-R

2015 ◽  
Vol 13 (28) ◽  
pp. 7762-7771 ◽  
Author(s):  
Hiroaki Ishida ◽  
Shinya Kimura ◽  
Noriyuki Kogure ◽  
Mariko Kitajima ◽  
Hiromitsu Takayama
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Absolute Configuration ◽  
Wittig Reaction ◽  
New Method ◽  
Asymmetric Total Synthesis ◽  
Aldol Cyclization ◽  
The Absolute

The first asymmetric total synthesis of lycoposerramine-R was accomplished by a strategy featuring the stereoselective intramolecular aldol cyclization giving a cis-fused 5/6 bicyclic skeleton and a new method for the construction of the pyridone ring via the aza-Wittig reaction, thereby establishing the absolute configuration of the natural product.

scholarly journals 4-Step Total Synthesis of (−)-Pavidolide B

2020 ◽  
Author(s):  
Yaoqiu Zhu ◽  
Elkin L. Romero ◽  
Kolluru Srinivas ◽  
Elizabeth Noriega
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
One Step

(−)-Pavidolide B is a complex tetracyclic diterpenoid with seven contiguous stereocenters, and classical total syntheses have recently been reported. In this work, an annulation strategy of carbanion cascade reaction is formulated for accomplishing an asymmetric total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction is a tandem intramolecular Michael addition, which constructs two 5-membered rings and five stereocenters in a highly selective fashion in one step. This work represents one of the most efficient cases of total synthesis and demonstrates that synthetic access to complex therapeutic natural product can be greatly simplified.

scholarly journals 4-Step Total Synthesis of (−)-Pavidolide B

2020 ◽  
Author(s):  
Yaoqiu Zhu ◽  
Elkin L. Romero ◽  
Kolluru Srinivas ◽  
Elizabeth Noriega
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
One Step

(−)-Pavidolide B is a complex tetracyclic diterpenoid with seven contiguous stereocenters, and classical total syntheses have recently been reported. In this work, an annulation strategy of carbanion cascade reaction is formulated for accomplishing an asymmetric total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction is a tandem intramolecular Michael addition, which constructs two 5-membered rings and five stereocenters in a highly selective fashion in one step. This work represents one of the most efficient cases of total synthesis and demonstrates that synthetic access to complex therapeutic natural product can be greatly simplified.

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