Total syntheses of ?-lactone containing natural products: I. total synthesis of belactosin C II. synthetic studies toward spongiolactone

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Title: Total syntheses of ?-lactone containing natural products: I. total synthesis of belactosin C II. synthetic studies toward spongiolactone
Author: Cho, Sung Wook
Abstract: The recently isolated bacterial metabolites , belactosins A -C from a fermentation broth of Streptomyces sp . UCK14 , uniquely contain a ? -lactone dipeptide motif and exhibit anticancer activities . The enantioselective synthesis of ( - ) -belactosin C and derivatives was accomplished in a concise manner employing the tandem , Mukaiyama aldol -lactonizaton (TMAL ) process and test their bioactivities . . One approach involved a distal double diastereoselective TMAL reaction with a dipeptide glyoxamide , whereas a second approach involved amide coupling of a dipeptide with a ? -lactone carboxylic acid , obtained via the TMAL process employing a chiral silyl ketene acetal . Enzymatic assays showed that the belactosins act as the dual inhibitors of the proteasome and the thioesterase domain of fatty acid synthase . Spongiolactone which uniquely contains a cyclopentyl -fused ? -lactone was isolated in 1986 from Spongi -onellagracilis No biological activity have been reported for this compound ; however , the acylating potential of the resident ? -lactone warrants screening for potential activity . After many setbacks in the synthesis of spongiolactone , significant progress has been made . Importantly , NCAL process also enabled a concise construction of [3 .2 .0] -bicyclo ? -lactone , which is the key structure in the spongiolactone synthesis and only a few steps remained to complete the synthesis .
URI: http : / /hdl .handle .net /1969 .1 /ETD -TAMU -3121
Date: 2009-05-15

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Total syntheses of ?-lactone containing natural products: I. total synthesis of belactosin C II. synthetic studies toward spongiolactone. Available electronically from http : / /hdl .handle .net /1969 .1 /ETD -TAMU -3121 .

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