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9.9 Product Class 9: Furans

DOI: 10.1055/sos-SD-009-00244

König, B.Science of Synthesis, (20019183.

The chemistry of furans has been an active field of research for a very long time. There are several reasons for this activity. Furan (1), as one of the representative five-membered heterocycles, can be found in many naturally occurring compounds. Polysubstituted furans play an important role in organic chemistry since they are key structural features of important natural products[‌1‌] and pharmaceuticals, and they can be employed as versatile building blocks in synthetic chemistry.

Me 8888 Meeeeee eeeeeeeee eee eeeee eeeee eeeeeeeeee, 8-eeeeee eeee (eeeee-8-eeeeeeeeee eeee). Me 8888, eee eeeeeee eeeeeeeee ee eee eeeee eeeeeeee eee eeeeeeeee ee eee Meeeee, eee eeeeeee eee eeeeeeeee eeee eeeeeeeeeee eeeeeeeeeee ee eeeeeeeee eeee.[‌8‌‌8‌]

Mee eeeeeeeeeeee ee eeeee eeeeeeeeeee eeeeeee eee eeeee eeeee eee eeeeeeeeeeee eeeeeeeee (Meeeee 8). Meeeeee eeeee eee eeeee eee eeee eee eeee eeeeeeeee.

Meeeee 8 Meeeeeeee ee eee Meeee Meeeeeee

Mee eeee eeeeeeeee eeeee eeeeeeeeee ee 8-eeeeeeeeeee (eeeee-8-eeeeeeeeeeee, eeeeeeee; 8) (Meeeee 8), eeeee ee eeeeeeee ee e eeeee eeeee ee eeeeee eeeeeeeeee ee eeeeeeeeeeee-eeeeeeeeee eeeeeee eeeeeeeee. Meeee eeeeeeeeeee eee ee eeeeeeee eeee eeeeeeeee eeeeeee eeeeeeeee, eeeee ee eeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeeee.[‌8‌‌8‌] 8-Meeeeeeeeee (8) eeeeee ee e eeeeeeeee eeeeeeee eeeeeeee eee eee eeeeeeeee ee eeee eeeee eeeee eeeeeeeeeee, eee eeee eeeeeeeee ee eeeee eee eeeeeeee eeeeeee [8-(eeeeeeeeeeeee)eeeee] eee 8-eeeeeeeeeee, eee ee eee eeee eeee eee eee eeeeeeeee eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeee. Meee eeeeeee eeeeeeee, eeeeeeeee eeeeeeee eeeeeeeeee, eeeeeee eeeee eeeee. Meeee ee ee eeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee ee eeee eeeeeeeee, eeeeeeeeeeeeeee, eeeeeeeeeee, eee eeeeeeeeeeee eeeeeeeee. Mee eeee eeeeeeeeeee eeeeeeeeee eee ee ee eee eeeeeeeeee ee eeeeeeeeeeeeeee, eeeeeeeee, eee eeeeeee. Meeeeeee eeee eeeeeee eeeee eeeee ee eeeee eeee eeeee eee eeeee ee eeeee eeeeee.[‌8‌] Meeee ee eeeeeeee eeeeeeeeeeee ee eee eeeeeeeeeeeeeee ee 8-eeeeeeeeeee eeee e eeeee eeeee eeeeeeee, eeeeeeeeee eeeeeeeee ee eeeeeeee.

Meeeee 8 Mee ee eee Meee Meeeeeeee Meeee Meeeeeeeeee:
8-Meeeeeeeeee

Mee eeeeeeeee ee eeeeee eee eeee eeeeeeee eeeeeeeeeee.[‌8‌‌88‌] Mee eeee eeeeee eeeeeeeeeeeee eeeeeee[‌88‌‌88‌] eee eeeeeeee eeeeeeee eeee eeee eeee ee eeee eee eeeeeeeee eeeeeeeee ee eeeee eeeeeeeee eeee eee eeeeeee ee eeee eeeeeee. M eeee eeeeeeeeeeee eeeeeeee ee eee eeeee ee ee 8888[‌88‌] eee eeeeee[‌88‌] ee eeeee ee eee eeeee eeeeeeeeee. M eeeeee ee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeeee eeeeeee eee eeeeeeee eeeeeeee.[‌88‌]

Meeee ee e eeeeeeeee eeeeee eeee e eeeeee eeee. Me eee e eee eeeeeee eeeee (88°M/888Meee) eee ee eeeeee eeeeeeeee. Me ee eeeeeeee eeee eeee eeeeee eeeeeee eeeeeeee, eee ee eeee eeeeeeee eeeeeee ee eeeee. Meeee eeeeeeeee eeee eeeeeeee eeeeeeeee eeeeeee eeee eee eeeeeeeeeeeeee ee eee eeee eeeeee π-eeeeeeeee eee eee ee eee eeeeee eeeeeeee eeeee.[‌88‌] Mee eeeeeeeeeee eeeeeeeee ee eeeee ee eeeeeeeee ee eeee eeeeeee, eee eeeeee eeeeee, eee MM eeeeeeee, eee 8MMMM eeeeeeee, eee eee eeee ee eeeeeeeeee. Mee eeeeeeeeee eeeeeeeee ee eeeee eee ee eeeeeeeee ee eeeeeee eee eeeee eeeeeeeee eeeeeeeeee (Meeeee 8), eeeeeee eee eeeeeee eeeeeeeeeeee ee eeeeeeee eee eeeeeeeeee π-eeeeeeee eeeeeee[‌88‌] eeeee eeee eee eeeeeee eeee. Meeee eee e eeeeee eeeeee ee 8.88×888 M·e (eeeeeee).[‌88‌]

Meeeee 8 Meeeeeeee Meeeeeeeee ee Meeee

Mee eeeeeeeeee ee eeeee eee eee eeeeeeeeeee eeee eeee eeeeeeeeeeee ee M-eee eeeeeeee,[‌88‌] eeeeeeee eeeeeeeeeee,[‌88‌] eee eeeeeeeee eeeeeeeeeeee.[‌88‌,‌88‌‌88‌] Mee eeeeee ee eeee eeeeee eee eeeeee eee eee eeeeee eeeeee[‌88‌] eeeeeee eeee eeeeeeeee eeeeeee eee eeeeeeeeee ee Meeee 8. Mee eeeeeeeee ee eee eeeeeeeeeeee eeee ee, ee eeeeeee, eee eeeeeee eeeeeeeeeeeee ee eeeeeeeeeeee, eee eeeee eeeeeeeeeeee ee eeee e eeeee eeeeee. Mee eeeeeeeeee eeeeeeeeeee ee eeeee eeeeeeee ee eeeee eeee-eeeeeeee eeeeeeeeeeeeee eeeeeeeee, eeee ee eeeeeee, eeeeeeeee, ee eeeeeeeeeee, eee eeeeee eee ee eee eeeeeeeee eeee ee eee eeeeeeeeeee. Mee eeeee eeee ee eeeeee eee eeee eeeee eeeeeeeeeeee ee eee eeeeeeeee ee eeeeeeee eeeeeeeeee, eeee ee ee [8.8](8,8)eeeeee-(8,8)-eeeeeeeeeeeeeeee,[‌88‌] ee eee eeeee eeeeeeeeeee eeeeeeeeee eeee eeeeeeeee.

Meeee 8 Meeeeeeeee Meeeeeeeee ee Meeee eeee Meeeeeeee Meeeeeeeee[‌88‌]

Meee Meeeee (Å) Meee Meeee Meee (e)
MM8 8.888(8) M8MM8 888.88(8)
M8M8 8.888(8) MM8M8 888.88(8)
M8M8 8.888(8) M8M8M8 888.88(8)
M8M 8.888(8) MM8M 888.88(88)
M8M 8.888(8) M8M8M 888.88(88)

Mee eeeeeeeeeeee ee eeee-eeeeeeeeeee eeeeee ee eeeeeeeeee ee eeeeeeeeee eee eeeeee eeeeeee.[‌88‌‌88‌] Mee eeeeeeee ee 8-eeeeeeeeeee eeee eeee eeeeeeeeeeee ee eeeeee.[‌88‌‌88‌]

Meeee-8-eee eee eeeee-8,8-eeeee eeee eeeeeeeeee eeee eee eeeeeeeeeeeee eee eeeeeeeee, eee eeeeeeeeeee (Meeeee 8).[‌88‌] Me eee eeee ee eeeee-8-ee eee eeeeeeeeeee ee eeeeeee eeeeee eeeeeeeeee ee eee eee eeeeeeee; ee eeeeeeeeee, eeeeeee eee eeeee eeeeeeeee eee eee eeeeeeeeee eeeeeeeeee.

Meeeee 8 Meeeeeeeee Meeeeeeeee ee Meeeeeee eee Meeeeeeeee[‌88‌]

Meeee ee e eeee eeeeeeeeeeeeeeeee eeeeee eeeeeeee. Meee eeeeeeeeeeeee ee eeeeeeee ee ee. 888°M ee eee eee eeeee.[‌88‌] Me eeeeeee eeee eeeeeee ee Meeee eeeee, eeeee eeeeeeeeeee eeeeeee eeee-eeeeeee eeeeeeeee, eeeee eee eeee ee eeeeeee eeeeeeeee.

Meeee eee ee eeeeeeeeee ee e π-eeeee eeeeeeee, eee eeee eeeeeeee ee eeeeeeeeeee ee eee ee eee eeeeeee eeeeeeeee eeeee eeeeeeeeeeeee eeeeeeeeeeee. Meeeeee, eee eeeeeeee ee eeeee ee eeeeeee eeeeeeee eeeeeeeee ee eeeeeeee eeee eeee ee eeeeeee, eeeeeee, ee eeeeeeeee.

Meeeeeeeeeeee eeeeeeeeeeee eeeeeeeee eee eee eeee eeeeeeeee eeeeee eee eeeee eeeeeeeeeeeeeeeee. Mee eeeeeeeee eeeeeeeeeeee ee eee 8- ee 8-eeeeeeeee ee eeee eeeeeee eeee ee eeeeeee ee eeeeeeeee. Mee eeeeee eeeeeeeeeeee eeeee eeeee ee eee 8-eeeeeeee eee ee eeee eeeeeeee eeeeeeeeee ee eee eeeee eeeeeeeeeee. Meeeeeeeeeee eeee eeee eeeeeeeee eeeeeee ee eee M8 eeeeeeee, e.e. eeeeeeee eeeeee ee eee eeeeeeee ee Meeee eeeee, eee ee eeeeeeeee ee eeee eee eeeee eeeeee ee M8.[‌88‌,‌88‌]

Meeeeeeeee ee eeeeee ee eeeeeee eeeeeeeee eee ee eeeeeeeeeee eeeeeeeeeeeee eeee eeee eeeeeeeeeeeeeeee.[‌88‌‌88‌] Meeeeeeee eeee eeeeeeeeeeee eeeee eeeeeeeeeee ee 8-eeeeeeeeeeee (8). Meee eee eeeee eeeeeeeeeee ee eeee, eeeee-8,8-eeeeeeeeeeeee (8) ee eeeeeeee (Meeeee 8). 8-Meeeeeeeeeee eee ee eeeeeeeee ee eeeeeeeeeeeeee eeeeeeee eeee 8-eeeeeeeeee. Meeeeeeeeeee eee ee eeee ee eeeeee eee eeeeeeeeee.

Meeeee 8 Meeeeeeeee ee Meeee[‌88‌‌88‌]

Meeeeeee-eeeeeeeeeee eeeeee, eeee ee 8-eeeee- (8) eee 8-eeeee-8-eeeeeeeeeee (8) ee 8-eeeee-8-eeeeeeeeeee (8), eeeeeee eeeeeeeeeeee eeeeeeeeeeee eeeeeeeee (Meeeee 8).[‌88‌,‌88‌] Meeeeeeee ee eeeeee eeee eeeeeeee eeee ee eee eeee eeeee ee ee ee eeeeee eeeeeeeee eeeeeeeeee. Me eeeeeeeee ee eee eeeeeee-eeeeeeeee eeeeeeeeeeeeee ee eeeee eee eeeeee eeeeeeeee, eeeee eeeeee e 8:8 eeeee/eeeeee eeeeeeeee eeeeeeeee. Mee eeeeeeeee ee eee eeeeeee ee eeee ee ee eeeeeeeeeee eeeeeeeeeee eeeeeeeee, ee eeeee ee 8MMMM. Meeee eeeeeeeeee eee eeee ee eeeeeeeeee eeeeee eee eeeeee(MM) eeee.[‌88‌]

Meeeee 8 Meeeeeeeeeee Meeeeeeeeeee Meeeeeeee ee Meeeeeee-Meeeeeeeeee Meeeee[‌88‌,‌88‌]

Meeeeeeeeeeeee eee eee eeeee eeeee ee eeeeeeeee eeeeeeeee ee eeeeee. Meee eeeeeeeeeeeeee[‌8‌,‌88‌,‌88‌] eee eeeeeeeeeeeeee[‌88‌,‌88‌] MeeeeMeeee eeeeeeeee ee eeeeee eeee eeeeeeee-eeee eeeeeee, eeeeeee, ee eeeeee eee eee eeee eeeeeeeee eeeeeeeeeeeeee. Meeee eeee eeeeeeeee,[‌88‌‌88‌] eeee-eeeeeeee eeeeeeeeee,[‌88‌‌88‌] eeeeeee eeeee,[‌88‌,‌88‌] eee eeeeeeee ee eeeeeeeeeee eeeee[‌88‌] eeee eeee eeee ee eeeeeeeeee eee eeeeeeee eeeee ee eeeeeeeeeee eeee eeeeeeeeeeee eeeeeeeeee. Mee eeeeeeee ee eeeee eeee ee eeee eeeeeeeee 8-eeeeeeee eeeeeee eeeeee eeeee-eeeeeeee eeeee eee [8+8] eeeeeeeeeeeee.[‌88‌,‌88‌] Me eeeeeeee, eeeeee eee eee ee eeeeeeeeeee ee MeeeeMeeee eeeeeeeee eeee eeeeeeee eeeeeeeeeee eeee-8,8-eeeeee,[‌88‌‌88‌] eee eeeeeee eeeeeeee ee 8,8-eeeeee eeeeeeeeeeeee eee eeeee.[‌88‌‌88‌] [8+8] Meeeeeeeeeeeee eeee eeeeeee[‌88‌] eee eeee eeeeeeee eeeeeeeee (eee MeeeeeeMüeee eeeeeeee) eee eeeeeeeee eeeeeeeeeeeeeee.[‌88‌‌88‌]

Mee eeeee eeeeee ee eeeeeeee ee eeeeeee eeeeeeee, eeeee eeeeeee eeeee ee 8,8-eeeeeeee ee eeee 8,8-eeeeeeeeeeee eeeeeeeeeee.[‌88‌] Mee [8+8]-eeeeeeeeeeeee eeeeeeee eeee eeeeeee eeeeee eeeeee eeeeeeeeeeeee, eeeee eee eeeeee eeeeeeeee eeeeeeeeeeeee.[‌88‌] Me eeeeeee eeee eeeeeee eeeee, eeeeee eeee ee eeeee 8,8-eeeeeeeee. Meeee eeeeeee eeeeeeeeee eeeeee eee eeeeeee ee eeeee eeeeeee- eee eeeeeeeeeeeeeeee ee eeee-eeeeee eeeeeeee.[‌88‌,‌88‌] Meeeeeeeeeee, eee eeee eeeeeeeeeee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee ee eeeee ee eeeeeeeeeeeeeee. Meeeeeeee eeee eeeeeeee eeeeee eeeee eeeeee- eee eeeee-eeeee eeeeeeeeee ee eeeeee eeeeeeeee. Mee eeeeee eeee ee eee eeeee eeee eee ee eeeeeeee ee eeeeeeee ee eeeeee. Meeeeee eeeee eee eeeeeee eeee eeeeeee ee 888°M eeeee eeeeeee, eeeeeee eee eeeeeeee eeee eeeeeeee eeeeeee, ee eee eeeeeeee ee eeeeeee ee 888888°M, eeeeee eeeeeeeee (eee Meeée eeeeeeee).[‌88‌] Meeeeee eeeee eeeeeeeeeee, eeee ee eeeeeeee, eeeeeee, eeeeee, eee eeeeeeeeeee, eee eeeeeeeee eeeeeeeee ee eeeeeeee eeeeeee ee eeee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeee ee eeeeee ee eeeeee 88%.

Meeeeeee eeeeeeeeeeeee eeeeeeeeee ee eeeee eee eeee eeeeeeeeeee eee eeeeeeeeee eeeee.[‌88‌‌88‌] Mee eeeeeee ee MM[‌88‌] eee eeee eeeeeeeeeeeee eeeeeeeeeeeeee[‌88‌] ee eeeeee, eee eeeeeeeeee.

Meeee: MM (MeMM) λeee, ee (ε): 888 (8888);[‌88‌] 8MMMM (MMMe8, δ): 8.88 (8M, 8-M, 8-M), 8.88 (8M, 8-M, 8-M);[‌88‌] MMMM eeeeee: M8,8=8.88Me, M8,8=8.88Me, M8,8=8.8Me, M8,8=8.8Me;[‌88‌] 88MMMM (eeeeeee-e8, δ): 888.8 (e, M8, M8), 888.8 (e, M8, M8).

8-Meeeeeeeeee: MM (MeMM) λeee, ee (ε): 888 (8888); 8MMMM (MMe8, δ): 8.88 (e, 8M, 8-M), 8.88 (ee, 8M, 8-M), 8.88 (e, 8M, 8-M);[‌88‌] 88MMMM (MMe8, δ): 88.8 (e, MMe), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8).[‌88‌]

8-Meeeeeeeeee: 8MMMM (MMe8, δ): 8.88 (e, 8M, Me), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M);[‌88‌] 88MMMM (MMe8, δ): 8.8 (e, Me), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8).[‌88‌]

8-Meeeeeeeeee: MM (MeMM) λeee, ee (ε): 888 (8888); 8MMMM (eeeeeee-e8, δ): 8.88 (ee, 8M, 8-M), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M); 88MMMM (MMMe8/MMe8, δ): 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M=M).[‌88‌]

8-Meeeeeeeee: MM (M8M) λeee, ee (ε): 888 (8888), 888 (8888); 8MMMM (eeeeeee-e8, δ): 8.88 (ee, 8M, 8-M), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M); 88MMMM (eeeeeee-e8, δ): 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8).

8-Meeeeeeeee: 8MMMM (eeeeeee-e8, δ): 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M).

8-Meeeeeeeeeee: MM (MeMM) λeee, ee (ε): 888 (8888); 8MMMM (MMMe8, δ): 8.88 (e, 8M, MMe), 8.88 (e, 8M, 8-M), 8.88 (ee, 8M, 8-M), 8.88 (e, 8M, 8-M)[‌88‌]; 88MMMM (MMMe8, δ): 88.8 (e, MMe), 88.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8).[‌88‌]

8-Meeeeeeeeeee: 8MMMM (MMe8, δ): 8.88 (e, 8M, Me), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M), 8.88 (e, 8M, 8-M);[‌88‌] 88MMMM (eeeeeee-e8, δ): 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8), 888.8 (e, M8).

Meeeee

MMMMMM:Meeee eeeeee ee eeeeeeeeeee eeeeeeeee. Meeeeee ee eee eee eeeeeee eeeee, e eeeeeeeee eeeeeeeeeeeee ee eeeee eee eeeee ee eeeeee eeeeee eeee eeeee eee eeeeeeeeee eeeeeeeeee. Meee eeeeeeeeeee ee eeeeee eeee eeeeeeeeeeeee eeeeeeee eee eeee ee ee eeeeeee eeee eeeee eeee. Meeeeeeeeeeeee[‌88‌,‌88‌] eeee eeee eeee ee eeeeee eeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeee eeeeeeeeeee eeee eeeeeeeeeeeee eeeeeeeeee.[‌88‌‌888‌]

References


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