Total Synthesis of the Marine Natural Product (−)‐Cribrostatin 4 (Renieramycin H) | Zendy

Chen Xiaochuan | Zendy; Zhu Jieping | Zendy

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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.

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