STEREOCHEMICAL CONTROL OF ANGULAR METHYLATION. A STEREOSELECTIVE TOTAL SYNTHESIS OF A 9,11-DEHYDROSTEROID

1957 ◽  
Vol 79 (5) ◽  
pp. 1261-1262 ◽  
Author(s):  
William S. Johnson ◽  
Duff S. Allen
Keyword(s):  
Total Synthesis ◽  
Stereochemical Control

scholarly journals Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

2013 ◽  
Vol 9 ◽  
pp. 2358-2366 ◽  
Author(s):  
Jie Zhang ◽  
Hong-Kui Zhang ◽  
Pei-Qiang Huang
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
Enantioselective Total Synthesis ◽  
Stereochemical Control ◽  
Stereoselective Addition ◽  
Methylmagnesium Iodide

A concise enantioselective synthesis of the advanced intermediate 5 for the synthesis of pumiliotoxins (Gallagher’s intermediate) is described. The synthesis started from the regio- and trans-diastereoselective (dr = 98:2) reductive 3-butenylation of (R)-3-(tert-butyldimethylsilyloxy)glutarimide 14. After O-desilylation and Dess–Martin oxidation, the resulting keto-lactam 10 was subjected to a highly trans-stereoselective addition of the methylmagnesium iodide to give carbinol 11 as sole diastereomer. An efficient ring closure procedure consisting of ozonolysis and reductive dehydroxylation provided the indolizidine derivative 5, which completed the formal enantioselective total synthesis of pumiliotoxins 251D and 237A.

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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