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- W3016457236 startingPage "1934578X2090917" @default.
- W3016457236 abstract "Spiroacetals are the central structural core element of numerous natural products and are essential for their biological activity. A typical structural representative of a spiroacetal is the bicyclic 1,6-dioxaspiro[4.5]decane ring system. It represents the complete or partial structure of many biologically potent natural products such as the Paravespula pheromone 1, the antibiotic (+)-monensin A 2, the anticancer agent (−)-berkelic acid 3, the antimitotic ingredient spirastrellolide F, characterized after methylation as (+)-methyl ester 4, and the marine toxin (−)-calyculin A 5. In these compounds, the 1,6-dioxaspiro[4.5]decane ring system is found in either spiro ( R)-6 or ( S) - 6 configuration. The corresponding 1,6,9-trioxaspiro[4.5]decane framework ( S)-7 and ( R)-7 with opposite chirality at the spiro center due to an additional oxygen atom at position 9 in the pyran portion has so far not been found in living organisms or been synthesized. To close this gap and enable structure–activity relationship studies, potentially leading to novel antibiotics and selective anticancer agents, we have developed an efficient and stereocontrolled route to the ( R)- and ( S)-configurated 1,6,9-trioxaspiro[4.5]decane ring system leading to oxa analog motifs of the above natural products." @default.
- W3016457236 created "2020-04-24" @default.
- W3016457236 creator A5016530309 @default.
- W3016457236 date "2020-04-01" @default.
- W3016457236 modified "2023-10-12" @default.
- W3016457236 title "Stereoselective Synthesis of 1,6,9-Tri-oxaspiro[4.5]decanes From <scp>d</scp>-Glucose: Novel Structural Motifs of Spiroacetal Natural Products" @default.
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- W3016457236 doi "https://doi.org/10.1177/1934578x20909175" @default.
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