scholarly journals Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

2014 ◽  
Vol 10 ◽  
pp. 2501-2512 ◽  
Author(s):  
Yiyang Liu ◽  
Marc Liniger ◽  
Ryan M McFadden ◽  
Jenny L Roizen ◽  
Jacquie Malette ◽  
...  
Keyword(s):  
Natural Product ◽  
Total Syntheses ◽  
Tertiary Carbon ◽  
Palladium Catalyzed ◽  
Target Molecules ◽  
Industrial Settings ◽  
Enantioselective Alkylation ◽  
Quaternary Carbons

Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

scholarly journals Development of a Second Generation Palladium-Catalyzed Cycloalkenylation and its Application to Bioactive Natural Product Synthesis

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Masahiro Toyota
Keyword(s):  
Natural Product ◽  
Second Generation ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Palladium Catalyzed ◽  
Oxidative Alkylation ◽  
Bioactive Natural Product

A novel palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins is described. This protocol was devised to solve one of the drawbacks of the original palladium-catalyzed cycloalkenylation that we developed. We call this new procedure the ‘second generation palladium-catalyzed cycloalkenylation’. This protocol has been applied to the total syntheses of cis-195A trans-195A boonein scholareins A C D and α-skytanthine.

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.

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Cascade Cyclizations ◽  
Palladium Catalyzed ◽  
Multiple Rings

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

Total Syntheses of Enokipodins A and B Utilizing Palladium-Catalyzed Addition of An Arylboronic Acid to An Allene

2009 ◽  
Vol 11 (6) ◽  
pp. 1441-1443 ◽  
Author(s):  
Masahiro Yoshida ◽  
Yasunobu Shoji ◽  
Kozo Shishido
Keyword(s):  
Arylboronic Acid ◽  
Total Syntheses ◽  
Palladium Catalyzed

Total Syntheses of Prothracarcin and Tomaymycin by Use of Palladium Catalyzed Carbonylation

Tetrahedron ◽  
1986 ◽  
Vol 42 (14) ◽  
pp. 3793-3806 ◽  
Author(s):  
Miwako Mori ◽  
Yasuhiro Uozumi ◽  
Masaya Kimura ◽  
Yoshio Ban
Keyword(s):  
Total Syntheses ◽  
Palladium Catalyzed

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 Palladium(II)-Catalyzed Efficient Synthesis of Wedelolactone and Evaluation as Potential Tyrosinase Inhibitor

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4130
Author(s):  
Huidan Huang ◽  
Jianqiu Chen ◽  
Jie Ren ◽  
Chaofeng Zhang ◽  
Fei Ji
Keyword(s):  
Natural Product ◽  
Raw Material ◽  
Coupling Reactions ◽  
Biosynthesis Pathway ◽  
Tyrosinase Inhibitor ◽  
Efficient Synthesis ◽  
Melanin Biosynthesis ◽  
Methodological Research ◽  
Palladium Catalyzed ◽  
Tyrosinase Inhibitors

Tyrosinase is an enzyme widely distributed in nature, which has multiple functions, especially in the melanin biosynthesis pathway. Despite the few clinically available tyrosinase inhibitors for whitening, a great demand remains for novel compounds with low side effects in terms of potential carcinogenicity and improved clinical efficacy. A natural product, wedelolactone (WEL), with a polyhydroxyl moiety, attracted our attention as a potential tyrosinase inhibitor. Before we studied the biological activity of the natural product, a synthetic methodological research was firstly carried to obtain enough raw material. WEL could be obtained efficiently through palladium-catalyzed boronation/coupling reactions and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)-involved oxidative deprotection/annulation reactions. Immediately after, the natural product was proven to be an efficient tyrosinase inhibitor. In conclusion, we developed a mild and efficient approach for the preparation of WEL, and the natural product was disclosed to have anti-tyrosinase activity, which could be widely used in multiple fields.

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