Stereocontrolled synthesis of substituted tetrahydrofurans

A) The addition of carbanions derived from chiral sulfoxides led to the stereocontrolled formation of β-hydroxysulfoxides for cyclization with net retention of configuration to yield highly substituted tetrahydrofurans.

Primary references: J. Am. Chem. Soc. 1981, 103, 7398-99; Tetrahedron 1986, 42, 3003-3011; Tetrahedron 1986, 42, 3013-3019.

B) The ocidation of benxylidene acetals to give intermediate orthoesters affords a stereocontrolled route to subtituted tetrahydrofurans.

Primary reference: J. Am. Chem. Soc.1984, 106, 2641.

C) A stereocontrolled approach for the synthesis of highly substituted tetrahydrofuran systems explored iodoetherification and related processes of chiral homoallylic alcohols and their corresponding ethers. These studies led to the total synthesis of citrocoviridin.

Primary references: Tet. Lett. 1985, 26, 2529-2532; Tet. Lett. 1986, 27, 2195-2198; J. Org. Chem. 1987, 52, 5067-5079.

Bis-homoallylic alcohols and the related epoxides were utilized for the stereocontrolled synthesis of substituted tetrahydrofurans.

Primary reference: Tet. Lett. 1984, 25, 5231-5234.

D) The stereocontrolled synthesis of cis-2,5-disubstituted-3-methylene tetrahydrofurans describes the use of p-allyl palladium intermediates.

Primary reference: Org. Lett.1999, 1, 1303-1305.

E) The preparation of enantioenriched 1,5-hexadiene bis-epoxides for synthesis of nonracemic 2,5-cis and trans-disubstituted tetrahydrofurans.

Primary reference: Heterocycles 2012, 84, 385-391.