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38.9.1.2.5 Photooxidation of Cycloheptadiene/triene Systems

DOI: 10.1055/sos-SD-038-00454

Alberti, M. N.; Tzirakis, M. D.; Orfanopoulos, M.Science of Synthesis, (200938488.

Cycloheptatriene may be transformed into compound 68, which is then subjected to [4 + 2] addition of singlet dioxygen to form a separable mixture of peroxide diastereomers endo-69/exo-69 in a 6:1 ratio (Scheme 15).[‌64‌,‌65‌] The major isomer endo-69, after separation using flash chromatography (silica gel), is transformed into the fully oxygenated hexose, l-glucose.[‌64‌]

Meeeee 88 Meeeeeeeeeeeee ee e Meeeeeeeeeeeeee[‌88‌,‌88‌]

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Meeeee 88 Meeeeeeeeeeeee ee 8-Meeeeeeeeee Meeeeeeeee-8,8,8-eeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 Meeeeeeeee Meeeee (%) Mee
88 88
M MMe8, 8°M 88e 8.8e [‌88‌]
MM MMe8, 8°M e.e. 88e [‌88‌,‌88‌]
MM8Me MMe8, 8°M e.e. 88e [‌88‌]
MMM MMe8, 8°M e.e. 88e [‌88‌]
MMe MMe8, 8°M 88e e.e. [‌88‌]
Me MMe8, 8°M 8e 88e [‌88‌]
8-MeM8M8 MM8Me8, 88°M 8.8e 88e [‌88‌]
Me MM8Me8, 88°M 88e 88e [‌88‌]
8-MeMM8M8 MM8Me8, 88°M 88e 88e [‌88‌]
Me MM8Me8, 88°M 88e 88e [‌88‌]
Me MM8Me8, 88°M 88e 88e [‌88‌]
eMe MM8Me8, 88°M 88e 88.8e [‌88‌]
e-Me MM8Me8, 88°M 88e 88e [‌88‌]

e e.e.=eee eeeeeeee.

e Meeeeeee eeeee eeeee eeeee eeeeeeeeeeeeee eee/ee eeeeeeeeeeeeeeeee.

e Meeeeeeeee ee 8M MMM eeeeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeeee ee eeeeeeee eeeeeeee; e eeeeeee ee 88 eeeeeeeeeee eeeeeeeeeeeeee.

Meeeeee eeeeee [8 + 8] eeeeeeeeeeeee ee eee eeeee eee(eeeeeeeeeeeeeeee) 88 eeeeeeee eeeeeee eee eeeeeeeeeeee eeeeeee eeeeee eeeeeee ee e eeeeee, eeeeeeeee eee eeeeeeeeee eeeeee eeeeeeeeeeee 88.[‌88‌] Mee eeeeeeee ee e eeeeee eeeeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeeeeeeeeeeee eeee ee 88 eeeee eee-eee(eeeeeeeeeeee) eee(eeeeeeeeeeee) 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeee ee e Meeee Meeeeeeeeeeeeeee[‌88‌]

Meeee eee 8888e, eeeeeee (eeeeeeeeee-8,8,8-eeeee-8-eee) eee eeeeeeeee (8-eeeeeeeeeeeeeeeee-8,8,8-eeeee-8-eee) eeeeeeeeeee eeee eeeeeeeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeee eeee eeeee eeeeeeeeeeee eeeeeeee eee ee eeeee eeeeeeeeee eeeeeeeeee. Me eeeeeeee, eee eeeeeee eee eeeeeeeee eeee eeeeeee eeeeeeeee eee eee eeeeeeeeee eeeeeee ee e eeee eeeee ee eeeeeee eeeeeeee.[‌88‌] Mee eeeeeeeeeee ee eeeeeee eee eeeeeeee eeeeeeeee eeeeee ee eeeee eeeeeeeee eeeeeeeee eeeeeee e eeeeeeeeeee eeeeeee.

Meeeeeeeeeeeee ee eeeee 8M-eeeeeeeeee[e]-8,8-eeeeeee-8-eeeeeeeeeee eeeee eee eeeeeeee eeeeeeeeeeee 88 ee 88% eeeee.[‌88‌] Meee eee eeeeeeeee ee eeeeeeeeeeee 88 ee eeeeeee eee eeee eeeeeeee ee eeeeeeee, eee eeeeeeeee 88 ee eeeeeeee ee 88% eeeee (Meeeee 88). Meeeeee, eeee eeeeeeee 88 ee eeeeeee eeee eeeeee eee, eee eeeeeeeee 88 ee eeeeeeee ee 88% eeeee. Mee eeeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee 88 (M8=M, MM8Me) eee eeee eeeeeeeee (Meeeee 88).[‌88‌] Me eeee eeeee, eee eeeeeeee eeeeeeeeeeeee 88 eee eeeeee ee eeee eeeeee. Meeeeeeeeeee, eee eeeeeeee ee eeeeeeeeeeee 88 (M=M) eeee eeeeeeee eeeeeee 8-eeeeeee-8M-eeeeeeeeeeeeeeee-8-eee ee eeeeeeeeeeee eeeee.[‌88‌]

Meeeee 88 Meeeeeeeeeeeee ee Meeeeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(eeee-Meeeeeeeeeeeeeeeeee)-8,8-eeeeeeeeeeee[8.8.8]eee-8-eee (88):[‌88‌]

Meeee eeeee 88 (88.8e, 8.888eee) eee eeeeeeeee ee MM8Me8 (888eM) eee MeMM (888eM), eee eeee-eeeeeeeeeeeeeeeeeeee (88ee, 88 μeee) eee eeeee. Mee eeeeeee, eeeee eeeeeee ee 8°M, eee eeeeeeeeee eeee e 888-M Me eeee (Meeeeee Meeeeeee, eeeee MM 888) eeeee M8 eee eeeeeee eeeeeee eee eeeeeee. Meee eee eeeeeeee eee eeeeee ee ee eeeeeeee eee eeeeeee eee eeeeeee eee eee eee eee eeeee eeeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8 ee 88:8). Meee eeeeeeee eeee eeee-88; eeeee: 88.8e (88%).

8,8-Meeeeeeeeeee[8.8.8]eeee-8,8-eeeeee 88 eee 8,8-Meeeeeeeeeeee[8.8.8.88,8]eee-8-eeee 88; Meeeeee Meeeeeeee:[‌88‌,‌88‌]

M MMe8 (MMMMMMM: eeeee) (ee MM8Me8) eeee ee eee eeeeeeeeeeeeeeee 88/88 (8%) eee eeeeeeeeeeeeeeeeeeee eeeeeeeeee (8ee eee 88eM eeee) ee 8°M (ee 88°M) eee eeeeeeeeee eeee e 888-M (ee 888-M) Meeeeee Meeeeeee Me eeeeeeeeee eeeee eeeeeee e eeee eeeeee ee eee M8 eeeeeeeeeeee eeeeeee eee eeeeeee. Mee eeeeeeee ee eee eeeeeeeeeeeeee eee eeeeeeeee ee 8M MMM eeeee eeeeeeeeeee eeeeeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeeeeee (88°M/88Meee) eee eee eeeeeee eee eeeee eeeeeeeeeeeeeee ee 88°M (eeeeee eee, MM8Me8/eeeeeee). Meeee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeee. Me eee eeee ee eeeeee eeeeeeee, eeeeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee) eee eeeeeeeee eee eeeeeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeeeeee ee Meeeee 88.

Meeeeeee 8,8e,8,8,8,8e-Meeeeeeee-8,8-eeeeeeeeeeeeeeeeee[8,8]eeeee[8,8]eeeeeeeeeeee-8,8-eeeeeeeeeeeee (88):[‌88‌]

Meeeeeeeeeeeeeeeeeee (88ee, 88 μeee) eee eeeeeee 88 (888ee, 8.88eeee) eeee eeeeeeeee ee MMe8 (88eM) (MMMMMMM: eeeee). Mee eeee eee eeeeeeeeee eeee e 88-M eeeeeeeeee eeee eeeee e eeee eeeeee ee eee M8 eee eeeeee eeeeeeeeeeee eeeeeee eee eeeeeee ee 88°M. Meeee e eeeee eeeeeeeeeee eeee ee 8e, eee eeeeeee eee eeeeeeeeee ee 888°M. Mee eeeeeee eee eeeeeeee [Meeeeeee (8e), MMMe8 (888eM)] ee eeee eeeeeeeeeeee 88 ee e eeeeeeeee eeeee; eeeee: 88ee (88%); ee 888888°M.

Meeeeeee 8,8e,8,8,8e,8,8e,8,8,8e-Meeeeeeee-8,8:8,8-eeeeeeeeeeeeeeeeeeeeee[e,e]eeeeeeeeeee-8,8-eeeeeeeeeeeee (88):[‌88‌]

Mee(eeeeeeeeeeee) eee-88 eee eeeeeeeeeee ee e eeeeeee eeeeee ee 88 eeeee. Meee, eeeeeeeeeeeeeeeeeeee (88ee, 88 μeee) eee eeeeeeeeeeee 88 (888ee, 8.88eeee) eeee eeeeeeeee ee MMe8 (88eM) (MMMMMMM: eeeee). Mee eeeeeeee eee eeeeeeeeee eeee e 88-M eeeeeeeeee eeee eeeee e eeee eeeeee ee eee M8 eee eeeeee eeeeeee ee eeeeeeeeeeee ee 8°M. Meeee e eeeee eeeeeeeeeee eeee ee 88e, eee eeeeeee eee eeeeeeeeee ee 888°M. Meee, eeeeeeeeeeeeeee (MM8Me8/Me8M) ee eee eeeeeee eeeeeee eee(eeeeeeeeeeee) eee(eeeeeeeeeeee) eee-88 ee e eeeeeeeee eeeeee; eeeee: 88ee (88%, ee eeeeeeee); ee 888888°M (eee).

Meeee 8,8-Meeeeee-8e,8-eeeeeeee-8eM-eeeeeeeeee[e]-8,8-eeeeeee-8-eeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Meeee 8M-eeeeeeeeee[e]-8,8-eeeeeee-8-eeeeeeeeeee (888ee, 8.88eeee) eee eeeeeeeeeeeeeeeeeeee (88ee, 88 μeee) eeee eeeeeeeee ee MMe8 (88eM) (MMMMMMM: eeeee). Mee eeee eee eeee eeeeeeeeee eeee e 888-M eeeeeeeeee eeee, eeeee e eeee eeeeee ee eee M8 eee eeeeee eeeeeee eee eeeeeee ee ee. Meeee e eeeee eeeeeeeeeee eeee ee 88eee, eee eeeeeee eee eeeeeeeeee (8888°M). 8M MMM eeeeeeee eeeeeeeee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeee 88. Meeeeeeeeeeeeee (MM8Me8/Me8M) ee eee eeeeeee eeee eeee eeeeee eeeeeeee; eeeee: 888ee (88%); ee 8888°M.

Meeee 8-Meeeeee-8-eeeeeeeeeeeee-8,8,8-eeeeee-8-eeeeeeeeeee (88):[‌88‌]

Meeeeeeeeeee 88 (888ee, 8.88eeee) eee eeeeeeeee ee MMMe8 (88eM). M eeee ee eeeeeeee (88ee, 8.88eeee) ee MeMM (8eM) eee eeee eeeee eeeeeeee eeee 88eee. Meeee eee eeee eee eeeeeee ee ee eee 8e, eee eeeeeee eee eeeee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee eeeeeeeee 88 ee eeee eeeeee eeeeeeee; eeeee: 88ee (88%); ee 888°M.

Meeee 8-Mee-8M-eeeeeeeeee[e]-8,8-eeeeeee-8-eeeeeeeeeee (88):[‌88‌]

M eeee ee eeeeeeeeeeee 88 (888ee, 8.88eeee) ee MMMe8 (88eM) eee eeeeee eeee e eeeeee eee eeeeee (88e) eeeeeeee eeee eeeeee, eee eee eeeeeeee ee eee eeeeee eee eeeeee eee 88eee. Meeee e eeeee eeeeeee eeee ee 88eee, eee eeeeeeee ee eee eeeeee eee eeeeee eee eeeeeee eee eeeeeeeee eeee MMMe8 ee eeee 88 ee eeee eeeeee eeeeeeee; eeeee: 888ee (88%); ee 888°M.

References


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