253156-60-4

Upstream product

• 186895-52-3 ethyl (2E,4S)-2,4-dimethyl-6-phenyl-2-hexenoate 
• 186895-53-4 (2E,4S)-2,4-dimethyl-6-phenyl-2-hexen-ol 
• 100348-15-0 (S)-2-<(2E)-1-chloro-2-butenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 186895-54-5 (2E,4S)-2,4-dimethyl-6-phenyl-2-hexen-1-al 

Downstream Products

• 253156-61-5 (1Z,3R,4R,5E,7S)-1-chloro-4-(tert-butyldimethylsilyloxy)-3,5,7-trimethyl-9-phenyl-1,5-nonadiene 
• 186895-59-0 ethyl (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-2,4,6,8-tetramethyl-10-phenyl-2,6-decadienoate 
• 186895-61-4 (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal 
• 186895-60-3 (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-2,4,6,8-tetramethyl-10-phenyl-2,6-decadienol 
• 186895-58-9 (2S,3R,4E,6S)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-8-phenyl-4-octanal 
• 186895-57-8 (2RS,3R,4R,5E,7S)-4-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3,5,7-trimethyl-9-phenyl-5-nonene 
• 186895-56-7 (3R,4R,5E,7S)-4-(tert-butyldimethylsilyloxy)-3,5,7-trimethyl-9-phenyl-1,5-nonadiene 

Relevant academic research and scientific papers

Synthesis of a C-9 to C-18 building block of the phenalamides

In the context of a synthesis of phenalamide A2, the C-9 to C-18 building block 6 was synthesized. The stereogenic centers were generated by alkylation of an Evans oxazolidinone 12 and by a crotylboration reaction using the enantiomerically pure (E)-α-chlorocrotylboronate (4).

Total synthesis of phenalamide A2

(formula presented) Phenalamide A2 (1b) has been synthesized for the first time. The synthesis features the homologation of aldehyde 5 to trienal 3 with the new conjunctive reagent 6 and the formation of amide 14 with the functionalized Horner-