An Efficient Stereoselective Synthesis of (±)-Sweroside and (±)-secologanin aglucone O-methyl ethers. Preliminary communication |
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Authors: | C. Richard Hutchinson,Kenneth C. Mattes,Masami Nakane,John J. Partridge,Milan R. Uskokovi |
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Affiliation: | C. Richard Hutchinson,Kenneth C. Mattes,Masami Nakane,John J. Partridge,Milan R. Uskoković |
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Abstract: | A seven-step stereoselective synthesis of (±)-sweroside aglucone O-methyl ether ( 16a ) was achieved in 27% overall yield from 1, 4-cyclohexadiene ( 4 ) and methyl diformylacetate ( 5 ). Secologanin aglucone O-methyl ether ( 18a ) was then formed from 16a in 90% overall yield by a straightforward process. The key step in the synthesis was a [2+2]-enone-photoannelation of 4 and 5 to form the key intermediate 6 which possessed the desired cis-fused ring configuration, and all the caron atoms needed to complete the synthesis of 16a and 18a . |
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