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1.8.2.11 Applications in the Syntheses of Natural Products and Drug Molecules

DOI: 10.1055/sos-SD-221-00221

Beccalli, E. M.; Bonetti, A.; Mazza, A.Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (20161454.

Application of the hydroamination of alkynes provides straightforward access to the nitrogen heterocyclic portion of (−)-quinocarcin, a pentacyclic tetrahydroisoquinoline alkaloid with antiproliferative activity against lymphocytic leukemia. Cationic gold complex 156 is used as catalyst to convert aminoalkyne 155 into 2a,3,4,5-tetrahydro-2H-furo[2,3,4-ij]isoquinolin-4-yl]pyrrolidine-2,4-dicarboxylate derivative 157. Control of the regioselectivity through a 6-endo-dig cyclization is fundamental to the success of this strategy (Scheme 69).[‌100‌]

Meeeee 88 Meeeeeeee ee e (−)-Meeeeeeeeee Meeeeeee ee Meee-Meeeeeeee Meeeeeeeeeeeee ee ee Meeeeeeeeee[‌888‌]

Meeeeeee, e eeee eeeeeeeeeee ee eeee eeeeeee ee eeeeeee ee eee eeeeeeeeeee ee eeeee[e]eeeeeeeeeeeeee eeeeeeeee eeee ee eeeeeeee eee e eeeeee eeeeeeee eeeee eeeeeeee ee eeeeeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeeee (e.e., 888) eeeeeee ee eeeeee eeeeee eeeeeeee ee Meeeeee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeeeee (e.e., 888) (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee e Meeeeeee Meeeeeeee ee Meee/Meeeee-Meeeeeeee Meeeeeeeeeeeee ee ee Meeeeeeeeeeee Meeeeeeee[‌88‌]

Mee eeeeeeeeeeeeee eeeeeeeeeeeeee eeeeeee eee eeeeee eeeeee eee eee eeeeeeeee eeeee eeeee ee eeeeeeeeeee eeeee 888, ee eeee eee eeeeeee eeeeeeeeeeee 888, ee eee eee eeee ee ee eeeeeeee ee eee eeeeeeeeee eeee ee eeeeeeeeee M, eeeee eeeeeee ee e eeeee ee eeeeeeeeeeee eeeeee Meeeeeeeeee eeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee e Meeeeeeeee M Meeeeeeee ee Meee/Meeeee-Meeeeeeee Meeeeeeeeeeeee[‌888‌]

Meeeeeeee-eeeeeeeee eeeeee eeeeeeeeee eeee eeee eeeeeeee ee eeeeeee eeeeeeeee eeeee ee eee eeeee eeeeeeeee ee e eeeeee ee eeeeeee eeeeeeee eee eeeeeeeeeeee eeeeee eeeeeeeee. Mee eeeeeeeeeee eeeeeeee (+)-eeeeeeeeeee M, ee eeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeeeeee eeeeeeeeee eeee ee eeeeeeeee eeeeeeee eeeeeee e eeeee eeeee ee eeeeee eeee eeeee, ee eeeeeeee eeeeeee eee eeeee- eee eeeeeeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeeee–eeeeeeeeeeee eeeeeee 888 eeee eeeeeeeeeeeee-eeeeeeeeeee eeeeeee-8-eeeeeeeeeee 888 eeeee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) eee eeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee ee Meeeeeeeeee M Meeeeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeee ee ee Meeeee[‌888‌]

Me eee eeeee ee eeeeeeeeeeee eeeeee eeeeeeeee, eeeeee-eeeeeeeee eeeeeeeeeeeeee eeeeeeeee ee eeee eeeeeee ee eeeeeee ee eeeeeeee β-eeeeeeeeeeee,[‌888‌] e eeeee ee eeeeeeeee eeee ee eeeeeeeee eeeeeeeee eee ee eeeee eeeeeeeeee ee eeee eeeeeeeeeeeee, eee eeee eee eee eeeeeeeeeee ee eeeeeee eeeeeeeee eeeeee eeee ee eee eeeeeeeeeeee[‌888‌] eee eeeeeeeeeee M.[‌888‌] Mee eee ee eeeeee eeeeeeeee ee eeeeeeeee; ee eeee, eee eeeeeeeeeee eeeeeeee eeee e eeeeeeeee eeeeeeee eeeee eeeee eee ee eee eeeeeeee ee eeeeeee eeeeeeee eeeeee. Mee ee eee eeee eeeeeeeeee eeeeeeee ee eee eeeeeeeeee ee eeeeee-eeeeeeeee eeee eeeeeeeee eee eeee eeeeeeee eee eee eeeeeeeeeee ee eeeeeeeeeee M, e eeeeee eeeeeeeee eeeeeeeeee, eeeee ee eeee eeee eeee M—M eeeee eee eeeeee eeee eeeeeeeee eeeeee eeeee eeeeeeeeee eeeeeeeeee (Meeeee 88). Me eeeeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeee eeeeee ee eeeeeee eee eee eeeeeeeeeeeeee M-eeeeeeeee ee eeee eeeeeeee ee eeeeeee eeeeeeeee eeeee, eeeee eee eeee ee eeeeeeee eeeeeeeee eee eeeeeeeeeeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee Meee M—M Meeee ee eee Meeeeeeee ee Meeeeeeeeee M[‌888‌]

M eeee eeeeeee ee e eeeeee-eeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee ee e eeee eeee ee eee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee (888, M8 = MMe)[‌88‌] eee eeeeeeeeeeeee (888, M8 = M),[‌88‌] eeeeee eeeeeeeeee ee eeee eeeee eeeeeee 88, ee eeeeeeeee eeeeeeeeeee eeeeee eee eeeeee eeeeeeeee. Mee eeeeeeeeeeeee eeee eeeeeeeeee 888 eee eeeeeeee ee eeeeeeeee ee eeeeee 888 eeee eeeeee(M) eeeeee, M,M,M′,M′-eeeeeeeeeeeeeeeeeeeeeeeeee, eee eeeeeeeee eeeeeeeee ee eeeeeee ee 888 °M (Meeeee 88).

Meeeee 88 Meeeee-Meeeeeeee Meeeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeee eee Meeeeeeeeeeee ee Meeeeeeee ee Meee Meeeeeee[‌88‌]

Meeeeeeeeee 88

M8 Meeee (%) ee 888 Mee
MMe >88 [‌88‌]
M  88 [‌88‌]

Meeeeeeeee, e eeeeee MMMMe/MMMe eeeeeeee eeeeeeeeee eeeee eeeeeeee eeeeeeee eeeeeeeeeee, ee eeeeeeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee eeee eeeeeeeee ee eeee eeeeee 888 ee eeeeee eee eee eeeeeeeeeeee 888 ee eeeeeeeeeee eeee (Meeeee 88).[‌888‌] Meeeeee eeeeee-eeeeeeeee eeee eeeeee eeeeeeeeee eeee eeee eeeeeee eee eee eeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeee ee eeeeeeeee M.[‌888‌]

Meeeee 88 Meeeee-Meeeeeeee Meeeeeeee ee ee Meeeeeeeeeee ee Meeeeeeeee ee Meeeeeeee ee ee Meee Meeeee[‌888‌]

Meeeeeeee-eeeeeeeee eeeeeeeeeeeeee eeeeeeeeee ee eeee eeeeeee eee eee eeeee ee eee eeeeeeeee ee eee eeeeeeee eeeeeee[‌888‌] eee eee eeeeeeeee eeeeeeee ee eeeeeeeeeeeee, eee ee eee eeee eeeeeeeeee eeeee eee eee eeeeeeeee ee eeeeeeee eee ee eee eeeeeeee eeeeeeeeeeee eeeeeee eeeeeeee ee eeeeeeeeeeeee. Me eeee eeee, 8-(8-eeeeeeeeeee)-8-(8-eeeeeeeeeee)eeeee-8-eee (888) ee eeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eee 8,8′-eee(eeeeeeeeeeeeeeeee)-8,8′-eeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeee eeeee eeeee eeeeee-eeeeeeee Meeeeee-eeee eeeeeeee eeeeeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee ee Meeeeeeeeeee ee Meeeeeeeeeeee ee Meeeeeeee ee ee Meee Meeeeee[‌888‌]

Meeeeeeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeeee M-(8-eeee-eeeeeeeeeee)eeeeeeeeeee 888, ee eeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeeee (MMM) eeeeeeeee, e eeeeee eeeeeeeee ee eeeeee eeeeeeeee eeee ee eeeeeeeeee, ee eeeeeeee ee eeeeeeee ee eeeeeeeeee eeeee 888 ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eee (M)-8,8′-ee-8,8-eeeeeeeeeeee-8,8′-eeeeeee(eeeeeeeeeeeeeeeee) [888, (M)-MMMMMMM] (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee ee Meeeeeeeeeee ee MMM Meeeeeeee[‌888‌]

M eeeeee eeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeeeeeeee eeeeeee ee ee eee eeeeeeeee ee eee eeeeeeee (+)-eeeeeeee,[‌888‌] eeeee eee eee eeeeeeeeee eeeeeeeeee[‌888‌] eee eeee eeeeeeee eeeeeeeee eeee eee eee eeeeeeeee eee eeeeeeeee eeeeeeee.[‌888‌] Me eeee eeee, eee eeeeeeeeeeee (8M,8M,8M)-8-eeeeee-8-(eeee-eeeeeeeeeeeeee)-8-(eeee-eeeeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee (888) ee eeeeee eeee eeeeeeeee 888 eee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eee eee[8-(eeeeeeeeeeeeeeeee)eeeeee] eeeee (888, MMMeeee) (Meeeee 88).

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee ee Meeeeeeeeeee ee (+)-Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeee (8M,8M,8M)-8-Meeeee-8-[(8eM,8M)-8e,8,8,8-eeeeeeeeee-8M-eeee[8,8,8-ee]eeeeeeeeeee-8-ee]eeeeeeeeeee-8,8-eeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee eeeeeeee eeeeeeeeeee-8,8-eeeeeeeeeeeee 888 (8.88 eeee) ee 8,8-eeeeeeeeeeeeee (8 eM) eeeee eeeee eee eeeee eee eeeeeeee eeee eeeeeeee 888 (8.88 eeee, ee eeeeeeee) ee ee. Mee eeeeeee eee eeeeee ee 88 °M eee eeeeeee eee 8 e. Meeee eee eeeeeee eee eeee eeeeee ee 8 °M, MeMM8MM (8.88 eeee), MeMM (8 eM), eee 8 M ee MMe (8.8 eM) eeee eeeeeeeeeeee eeeee ee eee eeeeeee. Meeeeeee eee eeeeeeeee eee 88 eee ee eeee eeeeeeeeeee. Mee eeee eee eeee eeeeeee eeee eee. ee MeMMM8 ee 8 °M eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eee eeeeee eeee eeeee eee eeeee (MeMM8). Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee ee eeee eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (M—M eeeeee eee, eeeeee/MeMMe 8:8) ee eeee eee eeeeeee ee e eeee eeeeee eee; eeeee: 88%.

eeee-Meeee 8,8-Meeeeeeee[8,8]eeeeeeeeeeee[8,8-e]eeeeeeeeeeeeee-88(88M)-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeeeeeeeeeeeeee 888 (8.88 eeee) ee 8,8-eeeeeeeeeeeeee (8 eM) eee eeeee e eeeeeee ee [(eeeeeeee-8-ee)-ee-eeee-eeeeeeeeeeeeee]eeeeeeeeee(M) (8 eee%), MeMMe8 (8 eee%), MeMM (8 eeeee), eee 8,8-eeeeeeeeeeeeee (8 eM) ee ee. Meeee eee eeeeeee eee eeee eeeeeee eee 88 e, eee. ee MeMMM8 eee eeeee eee eee eeeeeeeee eeeeeee eee eeeeeeeee eeee MMMe8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeeeee eee eeeeeee ee e eeeee eeeeee; eeeee: 88%.

Meeeee (8eM,88M,88eM,88M,88M)-8-Meeeee-88-eeeeeeeee-8,8e,8,88,88,88-eeeeeeeee-88M-88,88-eeeeeeeeeeeeee[8′,8′,8′:8,8]eeeeee[8,8-e]eeeeeeeee-88-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeeeee 8,8,8,8,8,8e,88,88e-eeeeeeeeeeeeee[e]eeeeee[8,8-e][8,8]eeeeeeeeeeeee-8-eeeeeeeeeee 888 (8.888 eeee) ee MM8Me8 (8.88 eM) eee eeeee MeMe(MMe8) (8 µeee) eee MeMMe (8 µeee). Mee eeee eee eeeeeee eeeeeeeee ee 88 °M eee eeeeeeeeeeee. Meeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) eeeeeeee eee eeeeeee ee e eeeee eeeee; eeeee: 88%.

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

M eeee ee Me8(eee)8•MMMe8 (8.88 µeee, ee eeeeeeee) eee eeeeee 888 (8.88 µeee, ee eeeeeeee) ee MM8Me8 (8 eM), eeeee eee eeee eeeeeee ee ee eee 88 eee, eee eeeee ee e eeeeeee ee M-eeeeeee-8M-eeeeeee-8-eeeeeeeeeee 888 (8.88 eeee) eee Me8MM8 (8.88 eeee) eeeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 88 e, eeee eeeeeeee eeeeeee e Meeeee eeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeee eeeeeeeee eeeee/Me8M 8:8, eeee MM8Me8/MeMM 88:8) ee eeee eee eeeeeee ee e eeeee eeeee; eeeee: 88%.

Meeeeeeeeee eee Meeeeeeeeeeee Meeeeeeeee 888; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeee 888 (88 µeee) ee eeeeeee (8.8 eM) ee e eeeeee eeee eee eeeee M8MM8 (8.88 ee, 8.8888 eeee). MeM (8.8 ee, 8.8 µeee) eee MMMMM (88 µeee) eeee eeeee eeeeeeeeeeee eee eee eeee eee eeeeee. Mee eeeee eeeeeeeeee eee eeeeee ee 888 °M eee 88 e eee eeeeeeee eeeeeee e eeee ee eeeeee eee, eeeeeee eeee MeMMe. Mee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeee) ee eeeee eee eeeeeee ee e eeeee eeeee.

eeee-Meeee (M)-8-(8-Meeeeee-8-eeeeeeee)-8-eeeeee-8-eee-8,8,8,8-eeeeeeeeee-8M-eeeee[e][8,8]eeeeeeeee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

eeee-Meeee 8-eeeeeeeeeeee 888 (8.88 eeee) eee eeeeeeeee ee eeeee MMM (88 eM). Me eeee eeee eeee eeeee eeeee M8MM8 (88.8 eeee) eee MeM (8.88 eeee). Meeee eee eeeeeeeee eeeeeee eee eeeeeee ee 88 °M eee 88 e eeeee M8, eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeee MMMe8 (88 eM) eee M8M (88 eM). Mee eeeeeee eeeee eee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (Me8MM8) eeeeee eee eeeeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8); eeeee: 88%.

8,88-Meeeeee-88M-eeeeeee[e,e]eeeeee-88-eee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8-(8-eeeeeeeeeee)-8-(8-eeeeeeeeeee)eeeee-8-eee (888; 8.888 eeee), Me(MMe)8 (8.888 eeee), MMMMM (8.888 eeee), eeeeeeeeee eeeeee M8MM8 (888 ee, 8.888 eeee), eeeeeee (8.8 eM), eee M8M (8.8 eM) eee eeeeee ee 888 °M. Meeee 8 e, eee eeeeeee eee eeeeeeeeeee eeeeeee M8M eee MM8Me8. Mee eeeeeee eeeee eee eeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (Me8M/MM8Me8 8:88) ee eeee eee eeeeeee ee eeeeee eeeeeee; eeeee: 88%.

(eM)-8-[8-(eeee-Meeee)eeeeee]-8,8-eeeeeeeeeeeeeee-8(8M)-eee (888); Meeeeee Meeeeeeee:[‌888‌]

Me8MM8 (8.8 eeee) eee eeeee ee M-(8-eeee-eeeeeeeeeee)-8-(8-eeeeeeeeee)eeeeeeeeeee (888; 8.8 eeee) ee eeeeeee (8.8 eM) eeeee eeeee. Meeee eee eeeeeee eee eeee eeeeeee eee 8 eee ee ee, eee eeeeeeeeee ee Me(MMe)8 (8.88 eeee) eee (M)-8,8′-ee-8,8-eeeeeeeeeeee-8,8′-eeeeeee(eeeeeeeeeeeeeeeee) (888; 8.888 eeee) ee eeeeeee (8.8 eM) eee eeeee. Mee eeeeeee eee eeeeeeeeee eeeeeee eee 88 e ee 88 °M, eeeeee eeee 8% ee MMe, eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe); eeeee: 88%; 88% ee.

(8M,8M,8M)-8-Meeeee-8-(eeee-eeeeeeeeeeeeee)-8-(eeee-eeeeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeeee-eeeee Meeeeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeee eeeee e eeeeee ee M8 eee eeeeeee eeee eeee-eeeee eeeeeeeee 888 (8.88 eeee), Me(MMe)8 (8 µeee), eee[8-(eeeeeeeeeeeeeeeee)eeeeee] eeeee (888, MMMeeee; 88 µeee), e-MeMMe (8.888 eeee), eee eeeeeeeeeeee (8.8 eeee). Mee eeee eee eeeeee eeee M8 eee eeeeeee (8 eM) eee eeeee ee eeeeeee. Mee eeeeeeeee eeeeeee eee eeeeee ee 88 °M eeee eeeeeeee eee 8 e eeeee eee eeeeeeee eeeeeeee eee eeee eeeeeeee, ee eeeeeeeeee ee MM eeeeeeee. Mee eeeeeee eee eeeeee ee ee, eee eee. ee MM8Me eee MeMMe eeee eeeee. Mee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeee 8.8:88.8) ee eeeeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 88%.

References


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