245678-56-2

Basic information

• Product Name: (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain
• CAS NO: 245678-56-2
• Molecular Weight: 431.445
• Mol File: 245678-56-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain(245678-56-2)
• EPA Substance Registry System: (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain(245678-56-2)

Safety Data

• Hazardous Substances Data: 245678-56-2(Hazardous Substances Data)

Upstream product

• 76240-25-0 7-benzyloxy-2H-1-benzopyran 
• 76240-26-1 (+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan 
• 61080-20-4 2-(chloromercurio)-4,5-(methylenedioxy)phenol 
• 14649-03-7 (S)-phenylethyl isocyanate 
• 2035-15-6 (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan 

Relevant articles and documents

Absolute configuration and total synthesis of (-)-cabenegrin A-I

The total synthesis of (-)-cabenegrin A-I [(-)-1] in five steps was achieved from (-)-6aR, 11aR-maackiain [(-)-5], which in turn was prepared by the optical resolution of racemic (±)-5 using S-(-)α-methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of(-)-maackiain [(- )-5] and (-)cabenegrin A-I [(-)-1] was proved by CD measurements. Synthesis of (±)maackiain [(±)-5] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.