Total Syntheses of Naturally Occurring Diacetylenic Spiroacetal Enol Ethers
β Scribed by Miyakoshi, Naoki; Aburano, Daisuke; Mukai, Chisato
- Book ID
- 127291733
- Publisher
- American Chemical Society
- Year
- 2005
- Tongue
- English
- Weight
- 179 KB
- Volume
- 70
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
i n addition to the already known 2-(2-thienylmethylene)-l,6dioxaspiro[4.S]dec-3-ene (l), a hitherto unknown thienyl-substituted spiroacetal enol ether was isolated from the subterranean parts of Arreniisia ludoviciana, the structure of which was eluci-
## Abstract The absolute configurations of three 6,7βoxygenated acetylenic spiroacetal enol ethers were determined by using the kinetic method of Horeau. The results were confirmed by the circular dichroism of the compounds in correlation with the corresponding 6,7βepoxide.
E)-and (Z)-2-methoxyca\_rbonylmethylene-l,6-dioxaspiro[4.5]decanes have been synthesized from an aeydie keto alcohol possessing an alkynoate past via intr, maoleculat conjugate addition. Unde~ thermodynamically controlled conditions using t-BuOK in THF, the (E)-isomer could be obtained in 52:1 ratio
Optically active 3,4-diacetoxy-2-formylmethylene-l,6-dioxaspiro[4.5]decanes have been synthesized from an acyclic keto-alcohol possessing an unsaturated aldehyde part via intmmolecular conjugate addition. The C3-and C4-ste~ogenic centers were introduced via Shatpless asymmetric dihydroxylation of an