Stereoselective Total Synthesis of Crassalactone A, a Natural Cytotoxic Styryl Lactone

2015 ◽  
Vol 98 (4) ◽  
pp. 509-514 ◽  
Author(s):  
Parigi Raghavendar Reddy ◽  
Biswanath Das
Keyword(s):  
Total Synthesis ◽  
Natural Cytotoxic

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone

Synlett ◽  
2017 ◽  
Vol 29 (04) ◽  
pp. 457-462 ◽  
Author(s):  
Mitsuru Kitamura ◽  
Dina Othman ◽  
Kota Otsuka ◽  
Shuhei Takahashi ◽  
Khalid Selim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Cyclization Reaction ◽  
Successful Strategy ◽  
Separation Of Diastereomers ◽  
Metal Catalyzed ◽  
Natural Cytotoxic

The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been ­accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-­catalyzed intramolecular cyclization reaction of the corresponding ­diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs–Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag2O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

First total synthesis of a new phenylpropanoid glycoside: natural cytotoxic compound from Cirsium japonicum

2017 ◽  
Vol 20 (12) ◽  
pp. 1154-1161 ◽  
Author(s):  
Hong-Bo Dong ◽  
Ming Hou ◽  
Wen-Bo Ma ◽  
Jing-Xia Zhang ◽  
Zhe-Yu Li ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Phenylpropanoid Glycoside ◽  
Cytotoxic Compound ◽  
Cirsium Japonicum ◽  
Natural Cytotoxic

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
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