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Organic & Biomolecular Chemistry

The international home of synthetic, physical and biomolecular organic chemistry.




Hot Article: Efficient synthesis toward macrolides


28 September 2009

US scientists are a step closer to synthesising two complex natural products after synthesising key subunits of their structure. 

Subham Mahapatra and Rich Carter, at Oregon State University, Corvallis, synthesised the western portion of amphidinolides C and F, macrolides with anti-cancer activity and a dense array of complex functionalities. 

C7-C20 subunit of amphidinolides

The pair had to use innovative methods to contruct the key structural motifs, explains Carter. These included a diastereoselective ring opening of an allylic vinyl iodide epoxide to set up the correct stereochemistry and a challenging sulfone alkylation-oxidation sequence. 

'Key future challenges include the development of a viable endgame strategy to complete the total syntheses of amphidinolides C and F which juggles the sensitive functional groups embedded within these compounds,' says Carter. 

Carter's long-term goal is to gain a better understanding of the macrolides' structure-activity relationship through analogue synthesis. He hopes this will lead to the development of new cancer chemotherapeutics. 

Joanne Thomson 

Link to journal article

Efficient synthesis of the C7-C20 subunit of amphidinolides C and F
Subham Mahapatra and Rich G. Carter, Org. Biomol. Chem., 2009, 7, 4582
DOI: 10.1039/b916744g


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