Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1387690 | Carbohydrate Research | 2016 | 5 Pages |
Abstract
•The first asymmetric total synthesis of marliolide from D-ribose is reported.•Formation of selenide and the subsequent radical deselenylation are reported.•Aldol reaction of dianion of a β-hydroxylactone with myristyl aldehyde is reported.
A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the β-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, β-hydroxyl γ-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Karabasappa Mailar, Won Jun Choi,