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.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

scholarly journals A new approach toward the total synthesis of (+)-batzellaside B

2012 ◽  
Vol 8 ◽  
pp. 1831-1838 ◽  
Author(s):  
Jolanta Wierzejska ◽  
Shin-ichi Motogoe ◽  
Yuto Makino ◽  
Tetsuya Sengoku ◽  
Masaki Takahashi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Pyroglutamic Acid ◽  
Acetoxy Group ◽  
Synthetic Approach ◽  
New Approach ◽  
Asymmetric Dihydroxylation

A new synthetic approach to (+)-batzellaside B from naturally abundant L-pyroglutamic acid is presented in this article. The key synthetic step involves Sharpless asymmetric dihydroxylation of an olefinic substrate functionalized with an acetoxy group to introduce two chiral centres diastereoselectively into the structure. Heterocyclic hemiaminal 4, which could be converted from the resulting product, was found to provide stereospecific access to enantiomerically enriched allylated intermediate, offering better prospects for the total synthesis of this 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.

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.

scholarly journals 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.

Total Synthesis and Structural Revision of Mycalol, an Anticancer Natural Product from the Marine Source

2015 ◽  
Vol 17 (7) ◽  
pp. 1652-1655 ◽  
Author(s):  
B. Seetharamsingh ◽  
P. R. Rajamohanan ◽  
D. Srinivasa Reddy
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Revision ◽  
Marine Source

ChemInform Abstract: Total Synthesis and Structural Revision of Mycalol, an Anticancer Natural Product from the Marine Source.

ChemInform ◽  
2015 ◽  
Vol 46 (34) ◽  
pp. no-no
Author(s):  
B. Seetharamsingh ◽  
P. R. Rajamohanan ◽  
D. Srinivasa Reddy
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Revision ◽  
Marine Source

Enantioselective total synthesis of colomitides and their absolute configuration determination and structural revision

2017 ◽  
Vol 15 (17) ◽  
pp. 3728-3735 ◽  
Author(s):  
Hongguang Yang ◽  
Xiaoyu Liu ◽  
Xiaoyu Li ◽  
Xiang Shi ◽  
Feilong Yang ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Synthetic Approach ◽  
Enantioselective Total Synthesis ◽  
Structural Revision

An efficient stereoselective synthetic approach to colomitides, 2,7-dioxabicyclo[3.2.1]octane-type natural products, is reported.

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