848986-16-3

Upstream product

• 1428585-56-1 2-(benzyloxy)-5-(4-(benzyloxy)-3,5-dimethoxyphenyl)-1,3-dimethoxy-6,7-dimethylnaphthalene 
• 1428585-51-6 5,5-bis(4-(benzyloxy)-3,5-dimethoxyphenyl)-4-methyldihydrofuran-2(3H)-one 
• 1355235-07-2 tert-butyl(((5R,6S)-5-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-1,3-dimethoxy-6,7-dimethyl-5,6-dihydronaphthalen-2-yl)oxy)dimethylsilane 

Relevant academic research and scientific papers

Triflimide-catalyzed allylsilane annulations of benzylic alcohols for the divergent synthesis of indanes and tetralins

The development of a triflimide-catalyzed annulation of benzylic alcohols with allylsilanes for the synthesis of indane or tetralin structures is reported. In this fragment coupling reaction, complexity is built rapidly from readily available starting materials to yield diverse sets of products with up to three contiguous stereocenters. Indanes or tetralins can be generated from common precursors depending on the structure of the allylsilane reagent used. The concise synthesis of several lignan natural products highlights the utility of this newly devised methodology.

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

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. The Royal Society of Chemistry 2013.

Total synthesis of (-)-sacidumlignans B and D

The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective α- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.