Synthesis of Narbonolide, muamvitin and (s) - (5)-[(s)-6-hyrdoxyoctyl]

The present invention provides methods and reagents relating to the PKS gene cluster for the polyketide antibiotics known as narbomycin and picromycin. Narbomycin is produced in Streptomyces narbonensis and both narbomycin and picromycin are produced in S. venezuelae. We have completed the formal synthesis of Narbonolide by using Yamaguchi esterification protocol. Muamvatin represents the first example of a naturally occurring 2,4,6-trioxaadamantane ring skeleton. Pulmonate molluscs of the genus Siphonaria are known for their characteristic production of polypropionate metabolites containing either a hydroxylated pyrone or ketal functionality. The formal synthesis of Muamvatin has been achieved in a stereocontrolled manner by silyltriflate mediated opening of epoxy alcohol and desymmetrization of the meso-bicyclic dihydrofuran using an asymmetric hydroboration. This synthetic sequence provides an easy access to the construction of the key fragments of Muamvatin.