An Efficient Stereoselective Synthesis of (±)‐Sweroside and (±)‐secologanin aglucone  O ‐methyl ethers. Preliminary communication | Zendy

Hutchinson C. Richard | Zendy; Mattes Kenneth C. | Zendy; Nakane Masami | Zendy; Partridge John J. | Zendy; Uskoković Milan R. | Zendy

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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 .

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