The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template

• 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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