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Synthetic study on naturally occurring acetylenic spiroacetal enol ethers: The first access to optically active 3,4-diacetoxy-2-formylmethylene-1,6-dioxaspiro[4.5]decanes

✍ Scribed by Hiroaki Toshima; Hisateru Aramaki; Akitami Ichihara

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 288 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00579-1

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✦ Synopsis

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 acyelic conjugated ketone with modified AD-mix-ct in high enantioselectivity (96% e.e.). This is the fhst access to optically active spiroacetai 2-enol ethers.

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✍ Hiroaki Toshima; Hisateru Aramaki; Akitami Ichihara 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

Synthetic Study on Naturally Occurring Acetylenic Spiroacetal Enol Ethers: The First Access to Optically Active 3,4-Diacetoxy-2formylmethylene -1,6-dioxaspiro[4,5]decanes. -In view of the interest in the synthesis of naturally occuring acetylenic spiroacetal enol ethers, the title spirodecanes are p