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.

Total Synthesis of the Antitumor Depsipeptide FE399 and its S-Benzyl Derivative: A Macrolactamization Approach

2020 ◽  
Author(s):  
Takayuki Tonoi ◽  
Miyuki Ikeda ◽  
Teruyuki Sato ◽  
Ryo Kawahara ◽  
Takatsugu Murata ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Condensation Reaction ◽  
Practical Method ◽  
Equilibrium Mixture ◽  
Conformational Isomers ◽  
Single Isomer

<div>An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.</div>

An Asymmetric Total Synthesis of Tupichilignan A using Donor-Acceptor Cyclopropanes: A Structural Revision of Tupichilignan A

2017 ◽  
Vol 6 (8) ◽  
pp. 977-980 ◽  
Author(s):  
Yumi Kimura ◽  
Yoshitomo Sone ◽  
Taichi Saito ◽  
Takehito Mochizuki ◽  
Yoshinori Nishii
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Structural Revision ◽  
Donor Acceptor

Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora

2015 ◽  
Vol 51 (28) ◽  
pp. 6202-6205 ◽  
Author(s):  
Matthew B. Calvert ◽  
Jonathan Sperry
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Synthetic Approach ◽  
Structural Revision ◽  
True Structure ◽  
Mimosa Tenuiflora

A bioinspired synthetic approach to nominal yuremamine has uncovered the true structure of the natural product to be a flavonoidal indole.

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.

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

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.

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

Total Synthesis and Structural Revision of a Harziane Diterpenoid

2019 ◽  
Author(s):  
Moritz Honig ◽  
Erick Carreira
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Spectral Characteristics ◽  
Tertiary Alcohol ◽  
Carbon Skeleton ◽  
Structural Revision ◽  
Stereochemical Analysis ◽  
Quaternary Stereocenter

The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.

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