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37.3.1.1.2.1 Variation 1: Regioselective Activation and Cyclization

DOI: 10.1055/sos-SD-037-00246

Griesbeck, A. G.; Sokolova, T.Science of Synthesis, (200837437.

As a prominent example for this approach, the synthesis of a Taxol analogue 23 involves the exposure of the Taxol derivative 22 that is mesyloxy-activated at the C5 hydroxy group to aluminum tri-tert-butoxide in benzene, efficiently promoting the regio- and diastereoselective (with inversion at C5) ring closure to 23 (Scheme 9).[‌34‌,‌35‌]

Meeeee 8 Meeeeeee Meeeeeee Meeeeee Meeeeeeeeee[‌88‌,‌88‌]

Meee e eeeeeeeeeeee eeee eeeeee, eeeeeeeeeeeeeeee eeee 8,8-eeee 88 eeeeeee eeee ee eeeee eeeeeeee ee e eeeeeeeee eeeeeeeeeeeeee eee eeeeeeeeee eeeeeeeee, eeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeee-eeeeeeee eeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee eeee eeeeeee 88 eeee eeeeeeeee ee eeeeeeeeeeeee ee M8 eeee eeeeee eeeeeee 88 eee 88% (Meeeee 88).[‌88‌] Mee eeeeeeeeeeeeee eeeeeeeeee ee e eeeeeeee eeeee eee eeeeeeeeeee ee eee M8' eeeeeeee ee e eeeeeeeeee eeeee ee eee eeeeeeeee ee [8.8.8]eeeeeeee eeeeeeeeeee eeee e eee-eeeeeeee (eeee eeeeeee ee eee eeeeeee eeee) eeeeeee eeee eeeeeeee M8' eee M8'.[‌88‌]

Meeeee 88 Meeee- eee Meeeeeeeeeeeeee Meeeeeeeeee ee 8,8-Meeee[‌88‌]

Me eeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeee ee e eeeeeee eeeeeee eeeee ee eee eeeeeeee ee e eeeeeeeee eeeeeee eeeee ee e 8,8 eeeeeeee ee eee eee ee eeeeeeeee eeeeeeeeeeeeeeeeeeeeee eee 8,8,8-eeeeeeeee-M-eeeeee-M-[(eeeeeeeeeeeeeee)eeeeeeee]eeeeeeeeeeeeeeeeee, eeeee eee eeee eeeeeeeee eee eee eeeeeeeee ee ee eeeeeee eeeeeeee eeeee eeeee ee e-eeeeeee ee eee eeeeee ee e Meeee eeeeeeeee.[‌88‌,‌88‌] Meeeeeeeeee ee eeee-, ee-, eee eeeeeeeeeeeeee 8,8-eeeee 88 eee eeeeeeeeeeeeee eeeeeeeeee eee eeee-eeeeeee eeeeeeeeeeee ee eeeeeeeee eeee eeeeee eeee-eeeeeeee ee eeeeeeeeeeeeeee eeeee eee eeeeeeee 88 (Meeeee 88).[‌88‌] Meee ee e eeeeeeee eeeeee eee eeeeeeeeee eeeeeee eeeeeee eeeeeeeeee eeeeee eeee eeeee eeeeeeeee eeee eee eeeeeeeee ee eee eeeeee eeee eeeeee eeee-eeeeeeee.

Meeeee 88 Meeeeee Meeeeeeee eeee Meeeeee Meeee 8-Meeeeeeeeeeeeeeee[‌88‌]

M eeeeeeeeeeeee eeeee 88 ee eeeeeeee eeee eee eeeeeeeeeee ee eee 8,8-eeee 88 ee e eeeee-eeee eeeeeeee ee eee eee: eeeeeeeeeeeee eeee 8.8 eeeeeeeeeee ee eeeeeeeeeeee eeeeeeee ee eeeeeeeeee ee eee eeeeeee eeeeeee eeeee eee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeee eeeee eeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeeee eeeeeee 88 eeee eeee eeeeeeeeeeeeeeeeeeee ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeee Meeeeee eeee e Meeeeee Meeeeeeee[‌88‌]

Me e eeeeeeee eeeeeeee eee eee eeeeeee 8,8-eeee eeeeeeeee, eeeee eeeeeeee (e.e., 88) eee ee eeeeeee (eeeeeeeee ee eee eeeeeeeeeee ee eeeeeee eeeeeeee). Meeeeeeeeeeeee eeee eeeeeee ee eeeee eeeeeeee eeee eeeeeee eeeeeeee (eeeeeeee ee eee eeeeeeeeeeee eeeeeee eeeee) eeeeeeeee 8,8-eeeee eeee eee ee eeee eeeeee ee eeeeeeeeee ee eee eeeeeee eeeeeee eeeee eee eeeeeeeeee eeee-eeeeeee eeeeeeeeeeeeee ee eeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeee Meeeeeee ee 8,8-Meee Meeeeeeeee eee Meeeeee Meeeeeeee[‌88‌]

Me eee ee eeeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeee-eeeeeeeeeeeeee eeeeeeeeee, eeeeeee-eeeeeeee eeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeeee (MMM) eee eeeeeeeee eee eee eeeeeeeeeee eeeeeee, eeeeeeee, eeeeeee, eee eeeeeee.[‌88‌] Mee eeee eeeeeeee (eeeeeeee eeeeeeeeee) eee ee eeeeeeeeeeee eeeeeee eee eee eeeeeeeee ee eee MM eeee ee eeeeeeeeee[‌88‌] eee eee eee eeeee eeeeeeeee ee eee eeeeeeee eeeeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

(M)-8-Meeeeeeee-8-eeeeeeeeeeeee [88, M8=(MM8)88Me; M8=Me; M8=M]; Meeeeee Meeeeeeee:[‌88‌]

Me e 8°M eeee ee eee eeee 88 (8.88e, 88eeee) ee MMM (88eM) eee eeeee e-MeMM (8.88e, 88eeee) ee eee eeeeeee eeeeeeee ee e eeee ee MeMe (8.88e, 88eeee) ee MMM (88eM) eeee 88eee. Mee eeeeeee eee eeeeeee eee 88eee eee eee 8-eeeeeeeeeeeeeeee eeeeeeeee eee eeeeeeeee ee MMM. Meeeeeeeee eeee eee MeMe eeee eeeee eeeee eee ee eee eeee eee eeeeeeee, ee eeeee eeeee e-MeMM (8.8e, 88eeee) eee eeeee. Meeee 88eee, eee eeeeeee eee eeeeeee eeee M8M (888eM) eee Me8M (888eM). Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8×888eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eeeeeeeeeeee, eee eeeeeeee ee eeeee eeeeeeeeeeeeee ee eeeeee eee eeeeeee 88 ee ee eee; eeeee: 8.88e (88%).

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