Funayama S, Cordell G A
J Nat Prod. 1985 Jul-Aug;48(4):547-54. doi: 10.1021/np50040a005.
The mechanisms of two acid-mediated coupling reactions of noracronycine (2) have been studied using deuterium-labeled acids. Dimerization of noracronycine (2) using D2SO4 afforded AB-1-d4 (8), whereas coupling 2 and dihydronoracronycine (3) in 10N DCl/MeOD (1:2.5) afforded dihydro AB-2-d8 (15). In addition, in the dimerization reaction of 2 using D2SO4-CH3OD (1:1) followed by dilution with D2O, AB-1-d16 (19) was obtained instead of 8. Initial protonation at the C2 position of noracronycine (2) was verified during these studies.
利用氘标记的酸研究了去甲克罗宁（2）的两种酸介导偶联反应的机制。使用D2SO4使去甲克罗宁（2）二聚化得到AB-1-d4（8），而在10N DCl/MeOD（1:2.5）中将2与二氢去甲克罗宁（3）偶联得到二氢AB-2-d8（15）。此外，在使用D2SO4-CH3OD（1:1）使2二聚化，然后用D2O稀释的反应中，得到的是AB-1-d16（19）而不是8。在这些研究中证实了去甲克罗宁（2）的C2位最初发生了质子化。
