
TY  - JOUR
A1  - Harvey, WE 
A1  - Miners, JO 
T1  - The Synthesis of Diepoxide Analogues of Fumagillin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 11
SP  - 2473
EP  - 2481
KW  - 
UR  - https://doi.org/10.1071/CH9792473 
N2  - Pathways from cyclohexanone to compounds of the general type 4-(1',2'-epoxy-1'-methylalkyl)- 1-oxaspiro[2,5]octane (5), the simplest diepoxide analogues of the antibiotic fumagillin (1a), are described. The sequence involves the initial formation of 6-acetyl-1,4-dioxaspiro[4,5]decane (2a) which is converted into a 2-alkenylcyclohexanone through the Wittig reaction. Subsequent spiro epoxidation of the cyclic ketone and peracid epoxidation of the side chain double bond affords the diepoxides (5a-c). In most respects the synthetic diepoxides possess the same stereochemistry as the equivalent functionality of fumagillin. 
ER  -

