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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A practical total synthesis of (+)-spirolaxine methyl ether
J S Yadav1, M Sreenivas, A Srinivas Reddy
1Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India. yadavpub@iict.res.in
Abstract:
An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.
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