Total synthesis of the marine natural product (-)-cribrostatin 4 (renieramycin H)

The cytotoxic title compd. (-)-cribrostatin 4 (I) 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 I was a domino sequence involving beta elimination and an intramol. phenolic Mannich reaction. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 46, 21, 3962-3965
Year:
2007
Keywords:
Note:
CAN 147:211659
26-9
Biomolecules and Their Synthetic Analogs
Institut de Chemie des Substances Naturelles,CNRS,Gif-sur-Yvette Cedex,Fr.
Journal
1433-7851
written in English.
77-76-9; 106-95-6; 111-31-9 (1-Hexanethiol); 60656-87-3; 62529-65-1; 95715-87-0; 686776-20-5; 925451-68-9 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. total synthesis of the marine natural product (-)-cribrostatin 4 via beta elimination and an intramol. phenolic Mannich reaction); 935268-15-8P; 935268-16-9P; 944941-62-2P; 944941-63-3P; 944941-64-4P; 944941-65-5P; 944941-66-6P; 944941-67-7P; 944941-68-8P; 944941-70-2P; 944941-72-4P; 944941-73-5P; 944941-74-6P; 944941-76-8P; 944941-77-9P; 944941-78-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. total synthesis of the marine natural product (-)-cribrostatin 4 via beta elimination and an intramol. phenolic Mannich reaction); 276682-85-0P ((-)-Cribrostatin 4); 944941-69-9P; 944941-71-3P; 944941-75-7P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. total synthesis of the marine natural product (-)-cribrostatin 4 via beta elimination and an intramol. phenolic Mannich reaction)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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