410080-90-9

Upstream product

• 144681-75-4 3-<(3,4-Dimethoxyphenyl)methoxy>propanal 
• 158466-49-0 3-(3,4-dimethoxybenzyl)oxypropan-1-ol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 590-18-1 (Z)-2-Butene 

Downstream Products

• 410080-91-0 (3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene 
• 144681-65-2 (2S,3S,5S,7R,8R,9S)-7-[2-(3,4-Dimethoxy-benzyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-vinyl-1,6-dioxa-spiro[4.5]decan-9-ol 
• 144681-65-2 (2S,3S,5S,7R,8R)-7-[2-(3,4-Dimethoxy-benzyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-vinyl-1,6-dioxa-spiro[4.5]decan-9-ol 
• 410080-96-5 (2S,3S,5S,7R,8S)-7-[2-(3,4-Dimethoxy-benzyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-vinyl-1,6-dioxa-spiro[4.5]decan-9-one 
• 144681-66-3 (2S,3R)-5-(3,4-dimethoxybenzyl)oxy-2-methyl-3-(tert-butyldimethylsilyl)oxypentanal 

Relevant academic research and scientific papers

Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.

Stereocontrolled Synthesis of Calyculin A: Construction of the C(15)-C(25) Spiroketal Unit

Two concise enantioselective syntheses of the C(15)-C(25) spiroketal unit of calyculin A, using derivatives of allyldiisopinocampheylborane efficiently to control 1,2- and 1,3-diol stereochemistries, are reported.