Use of Thiazoles in the Halogen Dance Reaction:  Application to the Total Synthesis of WS75624 B

2004 ◽  
Vol 69 (7) ◽  
pp. 2381-2385 ◽  
Author(s):  
Eric L. Stangeland ◽  
Tarek Sammakia
Keyword(s):  
Total Synthesis ◽  
Halogen Dance Reaction

Total Synthesis of Caerulomycin C via the Halogen Dance Reaction

2002 ◽  
Vol 4 (14) ◽  
pp. 2385-2388 ◽  
Author(s):  
Tarek Sammakia ◽  
Eric L. Stangeland ◽  
Mark C. Whitcomb
Keyword(s):  
Total Synthesis ◽  
Caerulomycin C ◽  
Halogen Dance Reaction

Total Synthesis of Lamellarins U and A3 by Interrupting Halogen Dance

Synthesis ◽  
2022 ◽  
Author(s):  
Yuya Okui ◽  
Yuto Yasuda ◽  
Atsunori Mori ◽  
Kentaro Okano
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Pyrrole Ring ◽  
Stille Coupling ◽  
Aryl Group ◽  
Negishi Coupling ◽  
Halogen Dance Reaction ◽  
Magnesium Exchange

A total synthesis of lamellarins U and A3 is described. The synthesis features interruption of a halogen dance reaction of a metalated α,β-dibromopyrrole. The pyrrolylmagnesium reagent, generated by deprotonative metalation using (TMP)MgCl·LiCl (TMP: 2,2,6,6-tetramethylpiperidide) as base, was transmetalated to the corresponding organozinc species without causing the halogen dance reaction, which underwent a Negishi coupling to incorporate an aryl group onto the pyrrole ring. The arylated α,β-dibromopyrrole was then converted into lamellarins U and A3 through an α-selective halogen–magnesium exchange followed by carboxylation and subsequent palladium-mediated cyclization. The late-stage introduction of another aryl group was performed using a Kosugi–Migita–Stille coupling to provide lamellarins U and A3.

ChemInform Abstract: Total Synthesis of Caerulomycin C via the Halogen Dance Reaction.

ChemInform ◽  
2010 ◽  
Vol 33 (48) ◽  
pp. no-no
Author(s):  
Tarek Sammakia ◽  
Eric L. Stangeland ◽  
Mark C. Whitcomb
Keyword(s):  
Total Synthesis ◽  
Caerulomycin C ◽  
Halogen Dance Reaction

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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