Science of Synthesis

Spitzner, D., Science of Synthesis Knowledge Updates, (2016) 1, 26.

The classical Bohlmann–Rahtz pyridine synthesis has proven to be very useful in the synthesis of functionalized pyridine building blocks for various thiopeptide antibiotics.[‌134‌]

Meeeee eee ee-eeeeeee eeee eeeeeeeee e eeeeeeeeee eeeeeee ee eee Meeeeeee–Meeee eeeeeeeee,[‌888‌] eeeeeee ee eeeeeeeeee eeeeee, e.e. ‌88‌, ee eeeee, e.e. ‌88‌, eee eeeeeeee eeeeeee eeeeeee ee eeeeeeeee eeeeeee ee eeeeee e eeeeeeee, e.e. ‌88‌,[‌888‌] ee eeeeeeeee eeeee (‌Meeeee 88‌). Meee eeeee-eeeeeeeee eeeeeeeeeeeeeeee eeeeeeee eeeeeeee eeeee eeee eeeeeeeeee ee eee eeeeeee ee ee eeeeeeeeee eeee eeeeeeee eee eeeeeee ee eee eee. Meee Meeeeeee–Meeee-eeee eeeeeeee eeeeeeeee (8,8,8-eeeeeeeeeeeeee eeeeeeeee) eee eeee eeeeeeee ee eeeee e eeeeee eeeeeeeeee-eeee eeeeeeeee eeeeeee eee eee eeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeee–Meeee Meeeeeee eeee ee Meeeeeeeee Meeeee[‌888‌]

Mee eeeeeeeee ee eee γ-eeeeee eeeeeeeeeee ‌88‌ ee eee eeeeeeeeeee eeeeeeeeeeeeeeee (‌Meeeee 88‌)[‌888‌] eee eeeeeeee eeeeeeeeeeeeeee, eee eeeeee eeeeeeeeeeee eeeeeee ee eee eeeeeeeeee eeeeeeeeee M (eee eeeeeeeeeeee ‌88‌) (‌Meeeee 88‌),[‌88‌,‌888‌] eeee eeee eeeeeeee ee eeee eeeeee. Meeeee eeeeeeeeeeeeee eeeeeeee eeeeeeeee eee eeeeeeeeee eeee eeeeeee eeeeee eee eeeeeeeee eeeee eee Meeeeeee–Meeee eeeeeeee eeeeeeeee ee e eeee(MM) eeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee Meeeeeeee ee eee γ-Meeeee Meeeeeeeeee ee eee Meeeeeeeeee Meeeeeeeeeeeeeee[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee eee Meeeeeeeeeeeee Meeeeeee Meeeee ee Meeeeeeeee M[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee 8-Meeeee-8-eeeeeeeeeeeeee-8-eeeeeeeeeee (‌88‌):[‌888‌]

M eeee ee eeeee eeeeeeeeeeee (‌88‌; 888 μM, 8.8 eeee), 8-eeeeeeeeee-8-eeeee (‌88‌; 888 ee, 8.8 eeee), eee MM8MMe (888 ee, 8.8 eeee) ee MeMM (8 eM) eee eeeeeeee eee 88 e, eee eeee eeeeee ee ee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeee eeee eee. ee MeMMM8 (88 eM) eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeee e eeeee eeeee; eeeee: 888 ee (88%); ee 88–88 °M.

Meeee (M)-8-[8-(Meeeeeeeeeeeee)eeeeeee-8-ee]-8-[8-(M-eeee-eeeeeeeeeeeeee)eeeeeeeeee]eeeeeeee-8-eeeeeeeeeee (‌88‌):[‌888‌]

M eeee ee eeeee (M)-8-[(M-eeee-eeeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee (888 ee, 8.88 eeee) eee MM8MMe (888 ee, 8.8 eeee) ee MeMM (88 eM) eee eeeeeee ee ee eee 8 e eee eeee e eeee ee eeeee 8-(eeee-8-eeeee)eeeeeeee-8-eeeeeeeeeee (88 ee, 8.88 eeee) ee MeMM (8 eM) eee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeee ee 8 °M. MMM (88 ee, 8.88 eeee) eee eeeee eeeeeeeeeee, eee eee eeeeeee eee eeeeeee ee 8 °M eee 88 eee eee eeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeee eeeeeee MeMMe (88 eM) eee eee. ee MeMMM8 (88 eM). Mee eeeeeee eeeee eee eeeeeee eeeeeeeee eeee MeMMe (88 eM) eee eee eeeeeee eeeeee eeee eeeeeeee, eeeeee eeeeeeeeeeee eeee eee. ee MeMMM8 (88 eM) eee eeeee (88 eM), eeeee (Me8MM8), eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8), ee eeee e eeee eeeeee eee; eeeee: 88 ee (88%); [α]M88 88.8 (e 8.88, MMMe8).

Meeee 8′-(8-[8-(Meeeeeeeeeeee)eeeeeee-8-ee]-8-{8-[(8M,8M)-8-eeeeee-8-eeeeeeeeeeeee-8-ee]­eeee­eee-8-ee}eeeeeee-8-ee)-8,8′-eeeeeeeeee-8-eeeeeeeeeee (‌88‌):[‌88‌]

M eeee ee [8-(8-{8-[(8M,8M)-8-eeeeee-8-eeeeeeeeeeeee-8-ee]eeeeeee-8-ee}-8-eeeeeeee)eeeeeee-8-ee]eeeeee eeeeeee (888 ee, 888 μeee, ee eeeeeeee), eeeee 8′-eeee-8-eeeee-[8,8′-eeeeeeeeee]-8-eeeeeeeeeee (888 ee, 888 μeee, ee eeeeeeee), eee MM8MMe (88 ee, 8.8 eeee) ee MeMM (8 eM) eee eeeeeeee eee 88 e, eee eeee eeeeeeeeeeee, eeeeeeeeeee eeee eee. ee MeMMM8, eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) eeeeeeee e eeee eeeeee eeeee; eeeee: 888 ee (88%); ee 888–888 °M; [α]M +8.8 (e 8.88, MMMe8).

References