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An Efficient Stereoselective Synthesis of (±)‐Sweroside and (±)‐secologanin aglucone O ‐methyl ethers. Preliminary communication
Author(s) -
Hutchinson C. Richard,
Mattes Kenneth C.,
Nakane Masami,
Partridge John J.,
Uskoković Milan R.
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610403
Subject(s) - chemistry , stereoselectivity , yield (engineering) , ether , enone , ring (chemistry) , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
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 .