Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction?

Organic & Biomolecular Chemistry Pub Date: 2013-02-12 DOI: 10.1039/C3OB00053B

Abstract

Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno–Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno–Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized.

Graphical abstract: Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction
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