Regio- and Stereoselective Allylic Substitutions of Chiral Secondary Alkylcopper Reagents: Total Synthesis of (+)-Lasiol, (+)-13-Norfaranal, and (+)-Faranal

2018 ◽  
Vol 58 (5) ◽  
pp. 1509-1514 ◽  
Author(s):  
Juri Skotnitzki ◽  
Lukas Spessert ◽  
Paul Knochel
Keyword(s):  
Total Synthesis ◽  
Allylic Substitutions

Application of allylic substitutions in natural products synthesis

2004 ◽  
Vol 76 (3) ◽  
pp. 495-505 ◽  
Author(s):  
G. Helmchen ◽  
Martin Ernst ◽  
G. Paradies
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Membrane Lipid ◽  
Pure Form ◽  
Allylic Alkylation ◽  
Allylic Substitutions ◽  
Synthesis Routes ◽  
Lipid Constituent ◽  
Natural Products Synthesis

Synthesis routes are described, allowing all known jasmonoids as well as their enantiomers to be synthesized in enantiomerically and diastereomerically pure form. The routes are based on a set of closely related lactones containing an electrophilic allylic moiety, which are accessible via asymmetric Pd-catalyzed allylic alkylation. Regio- and diastereoselective SN2'-anti-reactions of the electrophilic lactones with organocopper compounds furnished 2,3-cis-disubstituted cyclopentenones, which were further transformed into the target compounds, i.e., 12-oxophytodienoic acid (12-OPDA) in excellent overall yields. The methodology also allowed iridoids and isoprostanes to be prepared. The configuration of an Archaea membrane lipid constituent containing cyclopentane rings was determined by total synthesis of a diol that was also obtained by degradation of the natural product.

Total synthesis of Δ9(12)-capnellene-8α,10α-diol

1982 ◽  
Vol 23 (52) ◽  
pp. 5471-5474
Author(s):  
G Pattenden
Keyword(s):  
Total Synthesis

Total synthesis of melleumins A and B and their analogs: Determination of stereochemistry and Wnt signal inhibitory activity

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
M Ishibashi ◽  
S Hanazawa ◽  
Y Uchino ◽  
X Li ◽  
MA Arai
Keyword(s):  
Total Synthesis ◽  
Inhibitory Activity ◽  
Wnt Signal

Progress Toward The Total Synthesis Of The Marine Natural Product Karlotoxin 5

Planta Medica ◽  
2013 ◽  
Vol 79 (10) ◽  
Author(s):  
M Albadry ◽  
Y Zou ◽  
Y Takahashi ◽  
A Waters ◽  
M Hossein ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product

Formal Total Synthesis of Clausenamide

Synlett ◽  
1991 ◽  
Vol 1991 (04) ◽  
pp. 343-344
Author(s):  
Takayuki Yakura ◽  
Yukiko Matsumura ◽  
Masazumi Ikeda
Keyword(s):  
Total Synthesis

First Total Synthesis of Narceine Imide

2006 ◽  
Author(s):  
Axel Couture ◽  
Eric Deniau ◽  
Pierre Grandclaudon ◽  
Marc Lamblin
Keyword(s):  
Total Synthesis
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