Steven P. Tanis

A simple synthesis of 3-substituted furans. The preparations of dendrolasin, perillene and congeners

The Grignard reagent 7, derived from 3-chloromethyl furan, reacts with various alkyl- and allylic halides, in the presence of Li2CuCl4, to provide high yields of 3-substituted furans.

Furans in synthesis 4. Silyl furans as butenolide equivalents

Abstract The preparation and utilization of butenolide anion equivalents 5 and 6 in alkylation sequences is described. Treatment with CH 3 CO 3 H unmasks a latent butenolide moiety providing a general route to 3- and 4-alkyl 2(5H)-furanones.

A formal total synthesis of (±)-aphidicolin

A concise formal total synthesis of (±)-1 via the furan-terminated, epoxide-initiated cationic cyclization of 4 is described.

Furans in synthesis.7. A formal total synthesis of (+/−)-perhydrohistrionicotoxin

Abstract A formal total synthesis of (+/−)-perhydrohistrionicotoxin is reported. This sequence utilizes a regiospecific N -acyliminium ion initiated-furan terminated cyclization to construct the desired azaspiro[5.5]undecane ring system.

Furans in Synthesis. The Preparation of (±)-Lactaral

Abstract The Functionalized Grignard reagent 13 reacts with allylic chloride 14 , in the presence of Li 2 CuCl 4 , to provide lactarol-THP ether 15a which is subsequently converted to (±)-lactaral 5 in 72% overall yield from 13 .

A Study of the Diels-Alder Regioselectivity of Substituted Vinyl Cyclohexenes

Abstract The regioselectivity of dienes 6a and 6b in Diels-Alder reactions with ethylenic and acetylenic dienophilic was examined and found to be good-excellent. An improved synthesis of diene 6a via a CuSO4 mediated dehydration of the vinyl carbinol precursor is described.

Furans in Synthesis. The Preparation of Spiro-Cyclic Systems.☆

Abstract Furan-terminated cationic cyclizations allylic alcohols, enones, and N-acyl iminium ions as initiators have been explored as routes to highly functionalized spiro[4,5]decanes, spiro[5,5]undecanes, spiro[4,6]undecanes, and spiro[5,6]dodecanes.

Selective rearrangements of 4a,5-epoxides of 4,4-dimethyl-1,2,3,4,6,8a-hexahydronaphthalenes. ☆

Abstract Epoxidation selectivity of a number of 4,4-dimethyl-1,2,3,4,6,8a-hexahydronaphthalenes 4 were examined. Exposure of the isolated α-epoxides 7 provided excellent yields (79–92%) or rearranged fused indene-oxetanes 8 . Treatment of β-epoxides 5 with BF3·OEt 2 also yields oxetanes 8 and related alcohols 9 and 10 .