Total synthesis of cribrostatin IV: fine-tuning the character of an amide bond by remote control.
We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 --> 20).
Chan
Collin
C
Department of Chemistry, Columbia University, Havemeyer Hall, New York, NY 10027, USA.
Heid
Richard
R
Zheng
Shengping
S
Guo
Jinsong
J
Zhou
Bishan
B
Furuuchi
Takeshi
T
Danishefsky
Samuel J
SJ
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D007546:Isoquinolines / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry
D000577:Amides; D007546:Isoquinolines; C412688:cribrostatin 4