697234-90-5

Upstream product

• 501-53-1 benzyl chloroformate 
• 697234-89-2 (S)-2,2,2-trichloro-N-[1-[(3,6,7-trimethoxyphenanthren-9-yl)methyl]but-2-enyl]acetamide 
• 697234-88-1 2,2,2-trichloroacetimidic acid (R)-1-methyl-4-(3,6,7-trimethoxyphenanthren-9-yl)but-2-enyl ester 
• 585573-79-1 10-(bromomethyl)-2,3,6-trimethoxyphenanthrene 

Downstream Products

• 482-21-3 (R)-(-)-cryptopleurine 
• 697234-91-6 (S)-allyl[1-[(3,6,7-trimethoxyphenanthren-9-yl)methyl]but-2-enyl]carbamic acid benzyl ester 

Relevant academic research and scientific papers

Asymmetric Total Syntheses of (-)-Antofine and (-)-Cryptopleurine Using (R)-(E)-4-(Tributylstannyl)but-3-en-2-ol

The asymmetric total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, (-)-antofine and (-)-cryptopleurine, are described. An efficient synthetic pathway to the key intermediate 12, in enantiomerically pure form, was achieved by using a chiral building block (R)-9 and the Overman rearrangement with a total transfer of chirality. The problem of constructing the pyrrolidine and piperidine rings was successfully addressed, primarily by using a ring-closing metathesis reaction and a cross-metathesis reaction, respectively.