✦ LIBER ✦
An Efficient Stereoselective Synthesis of (±)-Sweroside and (±)-secologanin aglucone O-methyl ethers. Preliminary communication
✍ Scribed by C. Richard Hutchinson; Kenneth C. Mattes; Masami Nakane; John J. Partridge; Milan R. Uskoković
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- German
- Weight
- 277 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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.