Second Generation Palladium-Catalyzed Cycloalkenylation in Iridoid Lactone Synthesis: Total Syntheses of (±)-Onikulactone and (±)-Mitsugashiwalactone

Heterocycles ◽  
2010 ◽  
Vol 82 (2) ◽  
pp. 1705 ◽  
Author(s):  
Masahiro Toyota ◽  
Megumi Saeki
Keyword(s):  
Second Generation ◽  
Total Syntheses ◽  
Palladium Catalyzed ◽  
Lactone Synthesis

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.

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
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