Science of Synthesis

Lee, D.; O'Connor, M., Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (2015) 1, 99.

The prowess of enyne metathesis for the construction of multiply fused cyclic frameworks containing conjugated unsaturation is most clearly illustrated in the domino double ring-closing metathesis of dienynes containing appropriate tethers between the alkyne and alkenes (‌Table 2‌, entry 8).

Me ee eeeeeeee ee eeeeeeeeeeeeee M, eeeeee eeeee eeee-eeeeeee eeeeeeeeee ee eeeeeee ‌88‌ ee eeeeeeee ee eeeeeeee eee eeeeeeee eeeeeeeeeeeeee eeeeee eeeeeeee ‌88‌, eeeeeeeeee e eeeeeeeeee eeeeee eeeeee, ee eeee eeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Me eee eeeeee eeeeee eeee-eeeeeee eeeeeeeeee, eee eeeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeeeeeee eeeeeee eee eeeeeee eeeeee eee eeeeeeeeee eeeeeeeeeee ee eee eeeee-eeeeeeee eeeee eeeee eeeeeeee ee eee eeeeeeeeeeee eeeeee ee eeee e eeeeeeeeeee eeeeeeeeee ‌88‌. Meee eeeeee eeee eeeeeeeee eeeeeeeeee eeee-eeeeeee eeeeeeeeee ee eeeeeeee eee eeeeeeee eeeeeee ‌88‌. Mee eeeeeeeeee eee eeee eeeeee eeeeeeeeeee ee eeee eeeeee eeee eeeeee ‌88‌ eeee eeeeee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeee ee eee eeeeeee ee eeeeeeee eeeee eeeee ‌88M‌ eee eee eeeeeeeeeeee ‌88M‌. eeee-Meeeeeeeeeeeeeeeee eeeeeeeeee ee ‌88M‌ eee eeeeeeee ee eeeeee-eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeee eeeeee eeeeeeeeeeeeeeeeee eeeeeee, eeeee eeeeeee eee eeeee eeeee eee eeeeeee eee eeeeeeeeeee eeeee eeeee ee eeeeee ‌888‌ eeeeeeeee eeee-eeeeeeeeeeeeeeeeee eeeeeeeeeeee. Meeeeeeee eeeeeeeee eeee eee 8,8-eeee eeeeee ee ‌888‌ eeeeeeee ee Meee–Meeeee eeeeeeeee ee eee eeeeeeeee eeeeeeeee eeeeeee eeee eeeeeeeee ee eeeeeeee eeeeeeeeeeee ‌888‌ eeee eeeee Meeeeeeeeee eeeeeeeee e eeeee eeeeeeeee ee eeeeeeeeeeeeee M.[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeeee M[‌88‌,‌88‌]

M eeeeee eeeeeeeee ee eeeeeeee M eeeeeeee e eeeeee eeeeee eeeee eeee-eeeeeee eeeeeeeeee eeeeeeee ee e eeeeeeee ee eeeeeeeee eee eeeeeeee eeeeeee eeee (‌Meeeee 88‌).[‌88‌] Meee eeeee ‌888‌ ee eeeeeee eeee Meeeee–Meeeeee eeeeeeeee ‌888‌, e eeeeeee ee eeeeeeeeeeeeee Δ8,8-eeeeeeeeee-8,88-eeee eeeeeeeeee ‌888M‌/‌888M‌ ee eeeeeeee ee eeee eeeee. Me eeeeeeee eee eeeeee eeeeeee eeeeeeeeeee ee eee eeeeeee eeeee, e eeeee-eeeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeeee eee eeeeeeee eeeeeeeeeee eeeeeeeeee ‌888‌. Meee eeeeeee eeee eeeeeee eee eeeeee eeeeee eeeee eee eeeeeeeeeeee eee 8,8-eeeeeeeeeeeee eeeeee ee eeeeeeee eee eeeeeeeee eeeee, eeeeeee eee eeeeeeee eeeeeeee. Meee eeeeee, eee eeeeeee eeeeeeeeeeee ‌888M‌ ee eeeeeeeee eeee eeeeeee eeeeeeeeee eeee-eeeeeeee ‌888M‌ eee ‌888M‌ eee ‌888‌ eee eeeeee eeeeeeee ee eeeeeeeeeeeee eeeeeeeeeeee ‌888‌. Mee eeeeeeeeeee ee eeeeeeeeeeee ‌888M‌ ee eeeeeeee M eee eeeeeee eeee eeeeeeee ee Meeeeeeeee eee ee-eeeeeee,[‌88‌] eee eeee e eeeeee eeeeeeeee ee eeeeeeee ee eeeeeee ee eeee eeeeeeee eeeeee eeeeee eeeee eeee-eeeeeee eeeeeeeeee eeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeeeeee M[‌88‌]

Meeeeee eeee-eeeeeee eeeeeeeeee ee eeee ee eee eeeeeeeee ee (−)-eeeeeeeeeee eee (−)-eeeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Me eeee eeee, eee eeeeeeeeeee eeee ee eeeee eeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeee eeeeee eeeee eeee-eeeeeee eeeeeeeeee eee eeeee eeee-eeeeeee eeeeeeeeee. Me eee eee eeee eeeeeee ee eeeeeee eee eeeeee eeeeeeeeeeeeee eeeeeeeeeee eeeeee, eeeeeee ‌888‌ ee eeeeeee eeee eeeeeeeee ‌8‌ ee eeee eeeeeeeeeeeeeeeeeee ‌888‌ eeeeeee eee eeeeeeeee eeeeee eeeeeeeeee ‌888‌. Meee eeeeeee ee ‌888‌ ee eeee ‌888‌ ee eeeeeeee ee eee eeeeeeeeeee ee eeeeeeee eee eeeeee eeee. Mee eee eeeeeee eeeee eeee-eeeeeee eeeeeeeeee eeeeeeeee ee eeeeeee e eeeee eeee-eeeeeeee eeee, ‌888‌ ee eeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeeee ee eeeeee eeeeee ‌888‌, eeeee eeeee eeeeeeeeee e eeeeee eeeeeeeee, ee eeeeeeeee ee e Meeeeʼ eeeeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeeee ee eeee eeeeee ‌888‌. Meee-eeeeeee eeeeeeeeee ee ‌888‌ eeeeeeeee ‌888‌ eee eeee eeeee ee eeeeeeee ee ee eeee eeeeeee ee eee eeeeeeeee ee eeee ‌888‌. Meeeeeeeee 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee eeeeeeeee eeee eeeeeee eeeeeeeeeee, eeeee ee eeeeeee eeeeeeeee eeee eeeeeeeee ee eeeeeeeeeee e eeeeeeeeeeeee eeeee eeee eeeeeeeeeeeeeeee eee eeeeeeee eeee.

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

Mee eeee ee eee eeeeeee eeeeeeeeee eee eeee eeeeeeeeeee eeeeeeeee eeeeee eeeee eeee-eeeeeee eeeeeeeeee ee eee eeeeeee eeee-eeeeeee eeeee ee eeeeeeee eeeeeee e eeeeeeeeeeee eeeeee eeeee ee e eeeeeee eeee (‌Meeeee 88‌).[‌88‌] Meee, eeeeeeee eeeeeee ‌888‌ eeee eeeeeeeee ‌8‌ eeeeeee eeeeeeeeeee eeeeeeee ‌888‌ eee eee eeeeeeeee ee ee eeeeeee eeeeeeeeeee eeeeeeeee eeeeeeeeee ‌888‌ eeeeeeee ee ee eeeeeeeeeeeee eeeeee eeee-eeeeeee eeeeeeeeee eeee eee eeeeee eeeee. Meeeeee ee eee eeee-eeeeeeeeeeeeeeeeee eeeee eeee ‌888‌ eeeeeeeee eeee eeeeeee ‌888‌, e eeeeeeee eeee eeeeee ee e eeeeee eeeeeeeee eee eeeee eeeeeee eeeeeeeeee eeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeee Meeeeeeeeeee eeeeee. Meeeee, eeeee eee eeeeee eeeeeeeeeee ee ‌888‌ eeeeeee (+)-eeeeeee-8, eeeeeeeee ee eee eeeeee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeee eeeeeeee e eeeeeee ee (+)-eeeeeee-8 eee (+)-8-eee-eeeeeee-8 ee eeee eeeee eee 8.8:8 eeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeeeee Meeeeeeeee[‌88‌]

M eeeeeeeee-eeeee eeeeeeeee eeeeee eeeeeeee eee eeee eeeeeeeee eee eeeeee eeeeee eeeee eeee-eeeeeee eeeeeeeeee eee eee eeeeeeeeeeee ee M/M-8,8-eeeeee eeee eeee M/M eeeeeeeeeee eee eeeeeeeeee. Meee eeeeeeee ee eeeeeeee ee e eeeeeeeee eeeeeeee eeeeee eeeeeeeee M, e eeeeee eeee eeeeeeee ee M/M-8,8-eeeee eeeeee, ee eeee ee e eeeeeeeee ee eeeeeeeeeeee M eeeee e eeeeeee eeeeeeeeeeee eeeeeeee ee M/M-8,8-eeeee eeeeeeee eee e Meeee–Meeee eeeeeeee.[‌88‌] Mee eee eeeeeeeee ee eeeeeeeeeeee M, eeeeeee eeeeeeeee eeeeeee eeeeeeee eeeeee eee eeeeeeeeeeeeeeeeeeeee eeeeee eee eeeeee eeeeeeeee eeee eeeeeeeee ‌888‌ ee eee eeeeeeeeeee eeeeee eeeeeee eeeeeeeee eeeeeeeeeee eeeee. Meeeeeeeee eeeeeeeee ee ‌888‌ eeeee eeeeeee eeee-eeeeeee eeeeeeeeee eeeeeeeeee eeee Meeeeeʼ eeeeee-eeeeeeeeee eeeeeee ‌8‌ eeeeeeee ee eeeeeeeeeeee eeeeeeee eeeeeeee 8,8-eeeee ‌888‌ ee eeee eeeee, eeeee ee eeeeeee eeeeeeeeeee eeee ee eeeeeeee eeeeeeeeeeee ‌888‌.[‌88‌] Meeeeeee ‌888‌ ee eeeeeeeee ee eee Meeee eeeeeeeeeeee[‌888‌] eeee eee eee eeee eeeeee, eee eeee, e eeeeee eeeeeeeee ee (−)-eeeeeeeeeeee M ee eeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeee Meeeeeeee ee Meeeeeeeeeee M[‌88‌,‌888‌]

Mee eeeeeeeeee eeeeeeee eeeeeeeeeee ee eeeeeeeeeee eeeee eeeeeee eeee-eeeeeee eeeeeeeeee ee eee eeeeeee eeee.[‌888‌] Me eeeee ee ‌Meeeee 88‌, eeeeeee ‌888‌ eeeeeeeee eeeeee eeee-eeeeeee eeeeeeeeee, eeee eeeeee eeeeeeeee eeee eee eeeee-eeeeeeee eeeeeeee eeeeee, ee eeeeeeee e eeeeeeeeeee eeeee eeeeeeeeee ‌888‌, eeeee eeee eeeeee ee eee eeeeee eeee ee eeeeeee eeeee ‌888‌ eeeeeeeeee e M-eeeeeeeeeeeee eeeeee eeee eeeeee eee eeeee eeeeee eeee-eeeeeeee eeee. Meeee ‌888‌ ee eeeeeeee eeeeeeeeeeee eeeeeeeeeee ee eee M-eeeeeeeeeeeee eeeeee eeee ee eeeeee eeeeeeeeee ‌888‌. Meeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeee eeeeee eeee e eeeeee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeee 8-eeeeeeeeeeeee eeee, eeeeeeee ee e Meeeeee eeeeeeee eeeee eeeeee eeeeeeeeee eeee eeeeeeeeeeee, eeeeeeeee eee eeeeeeeee ee eeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeee[‌888‌]

Meee eeeeeeeeee-eeeee eeeeeeeee ee eeee eeeee eeee eeeee ‌888‌ ee eeeeeeeee ee e eeeee-eeeeeeeee eeee-eeeeeee eeeeeeeeee (‌Meeeee 88‌). Mee eeee eeeeeee eeeee ee ‌888‌ ee eee eeee eeee eeeeeeeee, eee ee eeee eeeeeeeee eee eeeeeeeeee ee eee eeeeee eeee ee ee, eeee eeeeeeeeeee eeeeeeeeee e eeeeeeeeeee eeeeeee ‌888‌. Meeeee eeeeee eeee-eeeeeee eeeeeeeeee eeee e eeeeeeee eeeeeeeeeeee ‌888‌ eeeeeeee ee eeeeeeeeee ee eee eeeeeee eeeee ee eee eeee-eeeeeeeeeeeeeeeeee eeeee eeeeee eeeee eeeeeeee 8,8-eeeee ‌888‌; eeee eeeeeeee ee eeeeeeeeee ee eeeeeeeee eeeeee ‌888‌ ee e eee-eeee eeeeeeee: (8) eeeeeeeee ee eee eeeeeee eeeeeee ee ‌888‌, eee (8) Meeee–Meeeeeeee eeeeeeeeee eeee eeeeeee ‌888‌ ee eeeeee M-eeeeee ‌888‌ eeeeeeeeeee. Meee eeeeeeee ee eeeeeee eeeeeeeeee eeee ‌888‌ ee eeeeeee ee eee eeeee eeeeee eeeeee eeee eee eeeeeeeee ee eee eeeeeeeee eeeeeee eeeee ee eeeeeeeee eee eeeeeeeeeeeeeee eeeeeeeee. Meeee eeeeeeeee ee ‌888‌ eeee (M)-eee-8-eeeee eeee ee (M,M)-eeee-8,8-eeeeeee eeee eeeeeeee ee eeee-eeeeeeeeeeeeee eeeeeeeeeeee eeeeeeee eee-eeeeeee M eee M, eeeeeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee eee-Meeeeee M eee M[‌888‌]

M eeeeeeeee ee (−)-eeeeeeeeee eeeeee ee eeeeeeeee eeeeeeeeee ee eeeee eeee-eeeeeee eeeeeeeeee eeee eee eeeeeeeeee eeeee-eeeeeeee eeeeee eeee ee eeeeeee ‌888‌ (‌Meeeee 88‌).[‌888‌] Meee eeeeeeee ‌888‌ eeee eee eeee eeeeeeee Meeeeee–Meeeee-eeee eeeeeeeee eeeeeee ‌888‌, e eeeeeeee eeeeeeeeeee eeeeeeeeee, e.e. ‌888‌, eeeee eeee eee eeee eeeeeee e eeeeee eeeeee eeee-eeeeeee eeeeeeeeee ee eeeeeee ‌888‌. Meeeeeee-eeeeeeee eeeeeee eeeeeeeee ee eee eeeeeeeee eeeeeeeee ee ‌888‌ ee eeeeeeee eee eeeeeee eeeeee ee ‌888‌, eeeeeeee ee eeeeeee eeeeeeeeeee eee eeeeeeeeee eeee eeeeeee eeee eeeeeee ee eee eeee-eeeeeeeeeeeeee eeeee, eeeeeee (−)-eeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee (−)-Meeeeeeeee[‌888‌]

M eeeeee eeeeee eeee-eeeeeee eeeeeeeeee eeeeeeee ee eeee eeeeeeee ee eee eeeeeeeee ee (±)-eeeeeeeeeeeee[‌888‌] (‌Meeeee 88‌) eee (±)-eeeeeeeeeee.[‌888‌] Mee eeeeeeeeeee eeee ee eeeee eeeeeee eeeeeeee ee eeeeeeee eeee eeeeeeee eeeeeee eeeeeeeeeeeee ‌888‌ eeee Meeeee eeeee-eeeeeeeeee eeeeeee ‌8‌. Meeeeeee eeeee eee eee eeeeeeee eeeeeee eeeeee ‌888‌, eee eeeeeee eeeeeee eeeeeeeeeeeee eeeee eeee eeeeeeeeee ee eee eeeeee eeee ee ee, eeee eee eeeeeeeeeee eeeeeeeeee ‌888‌ eeeeee eeee eeeeeeeeeee; eeee eeeeeee eeeee eeeeeeeeee eeeeeee eeee eee eeeeeee eeeeeeeeeeee ee eee eeeeeee ‌888‌ eeeee eeeeee eeee-eeeeeee eeeeeeeeee. Meee eeeeeee ee eee eeeeeee eeee ‌888‌, (±)-eeeeeeeeeeeee (‌888M‌) eee eee eeeeee ‌888M‌ eee eeeeeeee ee eeee eeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeee[‌888‌]

Meeee e eeeeeee eeeeeee, eeeee eeeeeeeee ee eeee eeeeeee ee eee eeeeee ee eeeeeeeeee eeeeeeeee eee eeeee eeee-eeeeeee eeeeeeeeee ee e eeeeeee eeee ee eeeeeeeee eee eeeeeeeeeeeeeeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌888‌] Me eeeeeeee eee eeeeee eeeeee eeee-eeeeeee eeeeeeeeee eeee ee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeeeee, e eeeee eeee-eeeeeee eeeeeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeee eeeeeeee eeeeeeeeeee eeeeeeeeee ‌888M‌ ee ‌888M‌. Meee, eeeeeeee eeeeeeeeee eeeeeee ‌888M‌ eee ‌888M‌ eeee e eeee eeeeeeee eeeeeee ee eee Meeeeee–Meeeee eeeeee-eeeeeeeeee eeeeeee ‌888‌ ee ee eeeeeeee eeeeeeeeeee eeeeeeee eeeeeee ‌888M‌ eee ‌888M‌, eeeeeeeeeeee, ee eeeeeee eeeeee. Meee eeeeeee eee eeeeeeeeee eeeeeeeeee ee (−)-eeeeeeeeeeeee (‌888M‌) eee (+)-eeeeeeeeeeeeeeeee (‌888M‌), eeeeeeeeeeee, eee eeeeeee eeeeeeeeeee eeeeeeee ee e eeeeeeeeeeee-eeeeeee M-eeeeeeeeee eeeeeeee. Meeeeeeeeeee, (+)-eeeeeeeeeeeeeeeee eee (−)-eeeeeeeeeeeee eee eeeeeeeee eeee (+)-eeeeeeeee M eee eeeeeeeee M, eeeeeeeeeeee, ee eee eeeeeeee eeeeeeeeeeee eeeeeee eeeeeee 8-eeeeeeeeeeeeeeeeeee eeee eeeeeeee eeeeeeeee ee eeee eeeeeeee eeeee ee eeeeeeeeee eeeeeeeeeeee ‌888M‌ eee ‌888M‌, eeee eeeeeee 8-eeeeeeeeeeeeeeeeeee eeee eeeeeeeee eeeeeeeeee eeeeeeeee (+)-eeeeeeeee M (‌888‌) eee eeeeeeeee M (‌888‌) eeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee eee Meeeeeeeee Meeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M,8M,8M,88M)-88-[8-(8,8-Meeeeeeeeeeee)-8,8-eeeeeee-8-ee]-8,88-eeeeeeeee-8-eeeeeeeeeeee-8,8-eeeeee Meeeeeee (‌888‌); Meeeeee Meeeeeeee eee Meeeee Meee-Meeeeee Meeeeeeeee eeee Meeeeeee:[‌88‌]

M eeee ee eeeeeee ‌888‌ (88 ee, 8.88 eeee) ee eee 8,8-eeeeeeeeeeeeee (8 eM) ee e Meeeeee eeee eee eeeeeeee eeeee eeeeee ee eee eeeeee–eeee–eeee eeeeee, eee eeeeeee eeee Meeeee eeeeee-eeeeeeeeee eeeeeeeee ‌8‌ (8.8 ee, 8.88 eeee). Mee eeeeeee eee eeee eeeeee ee 88–88 °M eee 8 e, eeeeeeee ee eeeeeee ee ee eee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee eeeeeee e eeeee eeee ee eeeeee eee (MeMMe/eeeeeee 8:8) ee eeeeee e eeeeeee ee eee eeeeeeee eeeeeeee, eeeeeeeeee eeeeeeee, eee eeeeeeeee eeeeeeeeeee eeeeeee. Meee eeeeeee ee MMM (8 eM) eee eeeeeeeee ee e eeee ee 8 M MMMM ee MMM (8.8 eM, 8.8 eeee) eee eeeeeeee eee 8–8 e. Mee eeeeeee eee eeeeee ee ee eee eeee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 88:88 ee 88:88) ee eeeeee eee eeeeeee ee e eeeeee eee; eeeee: 88.8 ee (88%).

References