Total synthesis of the marine natural product (-)-cribrostatin 4 (renieramycin H)
2007
Abstract
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)]
Details
Title
Total synthesis of the marine natural product (-)-cribrostatin 4 (renieramycin H)
Author(s)
Chen, Xiaochuan ; Zhu, Jieping
Published in
Angewandte Chemie, International Edition
Volume
46
Issue
21
Pages
3962-3965
Date
2007
ISSN
1433-7851
Keywords
Mannich reaction (intramol.; asym. total synthesis of the marine natural product (-)-cribrostatin 4 via beta elimination and an intramol. phenolic Mannich reaction); Stereoselective synthesis (total synthesis of the marine natural product (-)-cribrostatin 4 via beta elimination and an intramol. phenolic Mannich reaction); Elimination reaction (beta -; asym. total synthesis of the marine natural product (-)-cribrostatin 4 via beta elimination and an intramol. phenolic Mannich reaction); cribrostatin asym total synthesis elimination intramol phenolic Mannich reaction; renieramycin asym total synthesis elimination intramol phenolic Mannich reaction
Note
CAN 147:211659
26-9
Biomolecules and Their Synthetic Analogs
Institut de Chemie des Substances Naturelles,CNRS,Gif-sur-Yvette Cedex,Fr.
Journal
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)
26-9
Biomolecules and Their Synthetic Analogs
Institut de Chemie des Substances Naturelles,CNRS,Gif-sur-Yvette Cedex,Fr.
Journal
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
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25