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2.1.3 Applications in the Syntheses of Natural Products and Drug Molecules

DOI: 10.1055/sos-SD-222-00001

Xia, F.; Ye, S.Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (2016241.

Owing to the remarkable reactivity associated with three-membered rings, epoxides and aziridines play important roles in the synthesis of natural products and pharmaceutically useful molecules.

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Meeeee 88 Meeeeeeee ee (+)-Meeeeeeeeeee[‌88‌]

Me 8888, eee Meeeeeee eeeee eeeeeeeee e eeeee eeeeeeeee ee (−)-α-eeeeeeeee. Mee eee eeee ee eee eeeeeeee eeeeeeee eee eeeeeeeeeee ee eeeeeeeeeeee 88 eeeeeee eee eeeeeeeeee eeeeeeeeeee ee eeeeeeeeeee eeeeeee 88 eeeee e eeeeee eeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeeeeeee(eee)eeeeeeee(M) eee eeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee (−)-α-Meeeeeeee[‌88‌]

Me 8888, Mee eeeeeeee eeee e eeeeeeeee eeeeeee eeeeeeeee eee eeeeeeeeee eeeeeeeeeee ee eeeeeeeeee 88 eeeee eeeeeeee eeeeeeee ee eee eeeeeee ee eeeeeee eeeeeeeeeeeee eeeeeee 88 ee 88% eeeee eeee 88% ee. Meee eeeeee eeeeeee eee ee eeeeeee eeeeeeeee eeee eee eeeeeeeee eeee (M)-eeeeeeeeeeeee ee 88% eeeee eeee ee ee 88% ee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee (M)-Meeeeeeeeeeee[‌88‌]

Me 8888, Meeee eee Meee eeeeeeeee e eeeee eeeeeeeee ee (+)-eeeeeeeeeee M eeee eeeeeeeee 888 ee eee eee eeeeeeeeeeee. Me eee eeeeeeee ee [M-(8-eeeeeeeeeeeeeee)eeeee]eeeeeeeeeeeeee ee eee eeeeeee eeeeee, eeeeee–M-eeeeeeeeeeee eeeeeee eeeeeee 888 eeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeee 888 ee eeee eeeeeeeee 888 ee 88% eeeee, eee eeee eeeeeeeee eee ee eeeeeee eeeeeeeee eeee (+)-eeeeeeeeeee M ee eeee eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee (+)-Meeeeeeeeee M[‌88‌]

Mee eeeeeeeeeeeeeeee eeeee eeee (8M,8M)-β-eeeeeeeeeeeeeee ee e eeeeeeeeeee ee eeeeeee eeeeee eeeeeeeeeeee eeeeeee eeeeeeee eeee ee eeeeeeeeeee M eee eeeeeeeeee M eee M. Mee ee eeeee eeeeeee eeeeeee eeeeeeee eeee eeee eeeee ee eeeeeee eeeeee eeee-MMM eeeeeeee eee eeeee-eeeeeeee eeeeeeeeeeee. Me 8888, Meeeeeee eee Meeeee eeeeeeee eee eee ee Meeeeʼ eeeeeeeeeeee eeeeee 888 eee eee eeeeeeeeee eeeeeeeeeeeee ee eeeeeeeee eeeee 888, eeeeeeee ee e eeee-eeeeeee eeeeeeee eeee eeeeeeee ee eeee α-eeeee-β-eeeeeee eeeee 888 ee 88% eeeee eeee ee eeeeeeeeeeee eeeee ee >88:8 eee e eeeeeeeeeeeeee eeeee ee 88:8 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee (M,M)-β-Meeeeeeeeeeeeee[‌88‌]

Me 8888, Meeee eee Meeee eeeeeeeee eee eeeee eeeeeeeee ee (−)-eeeeeeeeeee ee eee eeeee ee eee eeeeeeeeee eeeeeeeeeeeee ee eeeeee eeeee 888. Meee eeeeeeee ee eeeeeeeee ee eee eeeeeeee ee 8-(eeeeeeeeeeeeee)eeeeee-8-eeeeeeeeeee ee eee eeeeeee eeeeee eee eeeeeeeee eeeeeee 88 ee eee eeeeeeee. Mee eeeeeeeeeeeee eeeeeeeee 888 ee eeeeeeee ee 88% eeeee eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee, eee ee eee ee eeeeeee eeeeeeeee eeee eee eeeeeee (−)-eeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee (−)-Meeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8-Meeeeeeeee[8.8.8]eeee-8-ee-8-ee Meeeeeeeeeeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeee-8,8-eeee-8-ee eeeeeeeeeeeeeeeeeeeeeeeee (88; 8.88 e, 8.88 eeee) ee MeMM (88 eM) eee eeeeee ee 8 °M eee eeee MM8MM8 (888 ee, 8.88 eeee) eee eeeee, eeeeeeee ee Me8MM8 (888 ee, 8.88 eeee). Mee eeeeeee eee eeeeeee eee 8 eee eee eeee eeeeeeee 88 (88 ee, 8.888 eeee) eee eeeee. Meeee eeeeeeee eee eeeeeee 8 eee, 88% M8M8 (8.8–8.8 eM, 8–8 eeeee) eee eeeee eee eee eeee eee eeeeeee eee ee eeeeeeeeee 8 e. Mee eeeeeee eee eeeeeee eeee Me8M eee eeeeee eeee eeeee (8 ×). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeee eeeeeeeeeeeeee (eeeeeee eeeeeee, Me8M/eeeeeee 8.8:88.8) eeee eee eeeee eeeeeeee; eeeee: 8.88 e (88%). Mee eeee eeee eeeeeeee eeeeee ee eeeeeeeee eeeee 88 eee ee ee; eeee, eee eeeeeeee eeee ee eeeeee ee eee eeeeeee ee e eeee ee eeeeeee (MMMMMMM: eeeeeeeeee) ee eeeeee eee eeeeeeee.

8-{(8M)-8-[(8M)-8-Meeeeeeeeeeeee-8-ee-8-ee]eeeeee-8-ee}eeeee-8-ee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeeee eee eee e eeeeeeee, eeeeeeeee eeee. Meeeeee eeeeeeee. Meeeee eeee eee eee eeeeeeee. Meeeeeeee eee eeeeeeeeee ee eee eeeeeeeeeee eeeee.

M eeeeeee ee MM(MeMe)8 (8 eM, 88 µeee) eee eeeeeeeeee eeee 88 (88.8 ee, 88 µeee) ee eeeeeee (8 eM) eee eeeeeee eee 8 e eee eeee eeeeee ee 8 °M. Meeeee eeeeeeeeeeeee (888 µM, 8.8 eeee) eee (M)-8-(8-eeeeeeeeeeeeee-8-eeee)eee-8-ee-8-ee (88; 888 ee, 8.8 eeee) eeee eeeee ee 8 °M. Mee eeeeeee eee eeeeeee eee 88 e, eee eeee (MeM)8M (888 µM, 8.8 eeee) eee eeeee ee eeee eeeeeeeeeee. Mee eeeeeee eee eeeeeee ee eeeee ee eee eee eeee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 88%; 88% ee.

(8eM,8eM)-8,8-Meeeeeee-8e,8e-eeeeeee-8M-eeeeeee[e][8]eeeeeeeeee-8-eeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M 8.88888 M eeee ee Me(MMe)8 ee MeMM (8.8 eM, 8.88 µeee) eee eeeee ee e 8.88888 M eeee ee eeeeee 88 ee MeMM (8.8 eM, 8.88 µeee) ee ee. Mee eeeeeee eee eeeeeee ee ee eee 8 e. Meeeeee 88 (8.88 eeee) eee MeMM (8.8 eeee) eeee eeeee ee eee eeee ee eee eeeeeeeee eeeeeee. Meee, eee eeeeeeeeeee eee eeeeeeeee ee 8 °M eee 88% M8M8 (8.88 eeee, eeeeeee eeee 8 eM MeMM) eee eeeee eeeeeeee ee eeeeeee eeee eeee 8 e. Mee eeeeeee eee eeeeeee ee 8 °M eee 8 e, eee eee eeeeeeee eee eeeeeeee ee eeeeee e eeeeeee ee 88% ee Me8M8M8 eee eee. ee MeMMM8 eeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%; 88% ee.

(8eM,8eM,8eM,8eM)-8-Meeee-8-eeeeeee-8-eeeee-8e,8e,8,8e,8,8e-eeeeeeeeeeeeeeee[8′,8′:8,8]eeeeeeeeee[8,8-e]eeeeeee[8,8-e]eeeeeee-8(8M)-eee (888); Meeeeee Meeeeeeee:[‌88‌]

Meeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eee eeeee ee e eeeeeee ee 8-Å eeeeeeeee eeeeee (88 ee), eeeeeeee 888 (88 ee, 8.888 eeee), MeMMMe (888 ee, 8.888 eeee), eee eeeeeeee 888 (88.8 ee, 8.8888 eeee) eeeee ee eeeeeeeeee ee M8. Mee eeeeeeeee eeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeeee eeeeeee e eeeeee eee eeee; eee eeee eee eeeeee eeee MeMMe. Meeee eeeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeeee eeeeeee, eeeeeeee 8; eeeeeeeee eeeee/MeMMe 8:8, 8:8, eeee 8:8) ee eeee e eeeeeeeee eeee; eeeee: 88.8 ee (88%).

Meeeee (8M,8M)-8-[8-(eeee-Meeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeeee-8-[(8-eeeeeeeeeee)eeeeeeeeeee]eeeeeeeeee (888); Meeeeee Meeeeeeee:[‌88‌]

Mee(eeeeeeeeeeeeee) eeeeee 888 (88 ee, 8.888 eeee), 8-Å eeeeeeeee eeeeee, eee MM8Me8 (8 eM) eeee eeeee ee Me(MMe)8 (88 ee, 8.888 eeee). Mee eeeeeee eee eeeeeee eeeee ee eeeeeeeeee ee M8 eee 88 eee. M eeee ee eeeee eeeee 888 (888 ee, 8.88 eeee) ee MM8Me8 (8 eM) eee eeeee ee eee eeeeeee, eeeeeeee ee [M-(8-eeeeeeeeeeeeeeeeeeee)eeeee]eeeeeeeeeeeeee (MeMMMe; 888 ee, 8.88 eeee), eee eee eeeeeeee eeeeee eee eeeeeee eeee M8. Mee eeeeeeee eee eeeeeee ee eeeeeee eeeee MeMMMe eee eeeeeeeeee eeeeeeeee (eeeeeeeee 8.8 e), ee eeeee eeeee eee eeeeeeee eee eeeeeee ee eeeeeeeeee eeeeeee e eeeee eee ee eeeeee eee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeeeee ee MeMM (8 eM). Mee eeeeeee eee eeeeeee eee 8.8 e, eeeee eeeee ee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeeeee e eeee eeeeee eee; eeeee: 888 ee (88%).

Meeee (8M,8M,8M)-8-Meeeeeeeeee-8-{[8-(eeeeeeeeeeeeee)eeeee]eeeeeeee}-8-eeeeeeeeee[8.8.8]eeee-8-eee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌88‌]

Meeee e eeeeeeee eeeeeeee ee M8, eeeee 888 (888 ee, 8.8 eeee), MeM (88 ee, 8.88 eeee), eee eeeeeeeee eeeeeee 88 (8.8 ee, 8.88 eeee) eeee eeeee eeeeeeeeeeee ee e eeee ee 8-(eeeeeeeeeeeeee)eeeeee-8-eeeeeeeeeee ee eeeeeeeeeeeee (8 eM). Mee eeeeeee eee eeeeee ee 8 °M. MeM(M8Me-Me)8 (888 ee, 8.88 eeee) eee eeeee ee eee eeeeeee. Mee eeeeeee eee eeeeee eeeeee ee ee eee eee eeee eeeeeee eee 8 e eeeee eeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee MMM. Mee eeeee eee eeeeeeee eee eee eeeeee eeeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eeeeee eeeeeee. Meeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8) eeeeeeeee eee eeeee eeeeeeee ee e eeeee eeee; eeeee: 888 ee (88%).

References