Synfacts 2006(5): 0412-0412  
DOI: 10.1055/s-2006-934401
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Wailupemycins B

Contributor(s): Philip Kocienski, Fiona Black
S. F. Kirsch, T. Bach*
Technische Universität München, Germany
Further Information

Publication History

Publication Date:
21 April 2006 (online)

Significance

Wailupemycins A and B inhibited the growth of E. coli in preliminary experiments. Both compounds feature highly substituted cyclohexanone rings making them challenging synthetic targets. They differ in configuration at C-7, which allows acetal formation to occur in Wailupemycin B only. Two approaches are described which failed at the stage of addition to a carbonyl. Wailupemycin B was eventually synthesized confirming the relative and absolute stereochemistry of the compound.