scholarly journals Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1610
Author(s):  
Yukari Sakagami ◽  
Naoki Kondo ◽  
Yuki Sawayama ◽  
Hiroyuki Yamakoshi ◽  
Seiichi Nakamura
Keyword(s):  
Natural Products ◽  
Functional Group ◽  
Lactone Ring ◽  
Side Chain ◽  
Total Syntheses ◽  
Epoxide Opening ◽  
Labdane Diterpene

Total syntheses of the labdane diterpene lactones marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereochemistries of desertine could be established by the transformations.

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

scholarly journals Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 249
Author(s):  
Raquel G. Soengas ◽  
Humberto Rodríguez-Solla
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Functional Group ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Bond Forming ◽  
Drug Candidates ◽  
The Past ◽  
Wide Range

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.

Balancing skeleton and functional groups in total syntheses of complex natural products: a case study of tigliane, daphnane and ingenane diterpenoids

2021 ◽  
Author(s):  
Zhi Liu ◽  
Zhengwei Ding† ◽  
Kai Chen ◽  
Ming Xu ◽  
Tao Yu ◽  
...  
Keyword(s):  
Natural Products ◽  
Functional Groups ◽  
Synthetic Chemistry ◽  
Total Syntheses ◽  
Strategic Balance

The fruitful advancement in synthetic chemistry of the title families of complex diterpenes has stimulated and enjoyed strategic balance between building the skeletons and installing the functional groups.

Vanadocene complexes of amino acids bearing functional group in the side chain

2013 ◽  
Vol 405 ◽  
pp. 121-127 ◽  
Author(s):  
Jaromír Vinklárek ◽  
Jan Honzíček ◽  
Milan Erben ◽  
Iva Klepalová ◽  
Aleš Eisner ◽  
...  
Keyword(s):  
Amino Acids ◽  
Functional Group ◽  
Side Chain

Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)-Pallambins A and B

2015 ◽  
Vol 127 (38) ◽  
pp. 11379-11382 ◽  
Author(s):  
Christian Ebner ◽  
Erick M. Carreira
Keyword(s):  
Natural Products ◽  
Total Syntheses

Asymmetric Hydrogenation of O-/N-Functional Group Substituted Arenes

2021 ◽  
Author(s):  
bingru shao ◽  
Lei Shi ◽  
Yong-Gui Zhou
Keyword(s):  
Natural Products ◽  
Functional Group ◽  
Asymmetric Hydrogenation ◽  
Biologically Active ◽  
Synthetic Methods

Asymmetric hydrogenation of aromatical compouds represents one of the most straightforward synthetic methods to construct important chiral cyclic skeletons that are often found in biologically active agents and natural products....

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