Corey's synthesis of pentacycloanammoxic acid

Background

        Fatty acid based derivatives of this target compound are major components of organelles in anammoxic microbes. These microbes use hydrazine and nitrite as intermediates en route to the production of energy. This is extraordinary because hydrazine is a major component of rocket fuel!

References

1. Mascitti, V.; Corey, E. J. Total Synthesis of (±)-Pentacycloanammoxic Acid, J. Am. Chem. Soc. 2004 126(48); 15664-15665. DOI: 10.1021/ja044089a
2. Mascitti, V.; Corey, E. J. Enantioselective Synthesis of Pentacycloanammoxic Acid, J. Am. Chem. Soc. 2006 128(10) pp 3118 - 3119. DOI: 10.1021/ja058370g