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.

meth1A

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.

meth1B

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.

meth1C

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.

meth1C2

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.

meth1D

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.

meth1E

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