Premium
Total Synthesis of the Marine Natural Product (−)‐Cribrostatin 4 (Renieramycin H)
Author(s) -
Chen Xiaochuan,
Zhu Jieping
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200700539
Subject(s) - domino , natural product , intramolecular force , sequence (biology) , yield (engineering) , key (lock) , total synthesis , stereochemistry , chemistry , core (optical fiber) , product (mathematics) , combinatorial chemistry , computer science , combinatorics , organic chemistry , mathematics , biochemistry , catalysis , telecommunications , physics , computer security , thermodynamics , geometry
Winning at dominoes : The cytotoxic title compound was synthesized from five readily available starting materials in a longest linear sequence of 21 steps and 4.3 % overall yield. The key step in the construction of the pentacyclic core of 1 was a domino sequence involving β elimination and an intramolecular phenolic Mannich reaction. Alloc=allyloxycarbonyl, Bn=benzyl, Boc= tert ‐butoxycarbonyl.