Patent ID: 6919465

Claim:
A method of preparing (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan comprising: (a) optionally reacting (5S)-hydroxymethyl-5H-furan-2-one with a compound capable of positioning a protecting group at the hydroxy position of (5S)-hydroxymethyl-5H-furan-2-one to provide a protected furan-2-one; (b) subjecting (5S)-hydroxymethyl-5H-furan-2-one or the protected furan-2-one of optional step (a) to a photochemical reaction in the presence of 1,3-dioxolane to provide a 1,3-dioxolan-substituted furan-2-one; (c) reducing the 1,3-dioxolane-substituted furan-2-one of step (b) to provide a reduced product, then hydrolyzing the reduced product to provide a product having a structure (d) oxidizing the product of step (c) to provide a product having a structure and (e) reducing the product of step (d) to provide (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]-furan.