A Convergent Approach to Cyclopeptide Alkaloids: Total Synthesis of Sanjoinine G1
Temal-Laieb, Taoues; Chastanet, Jacqueline; Zhu, Jieping
2002

Abstract

A general strategy for the synthesis of cyclopeptide alkaloids contg. an endocyclic aryl-alkyl ether bond has been developed featuring a key intramol. SNAr reaction. The importance of the N-terminal protective group in the realization of such a strategy is documented. From the appropriate amino acid constituents, the natural sanjoinine G1 (I), a 14-membered para-cyclophane, has been synthesized in seven steps with 21% overall yield. [on SciFinder (R)]

Details

Title A Convergent Approach to Cyclopeptide Alkaloids: Total Synthesis of Sanjoinine G1
Author(s) Temal-Laieb, Taoues ; Chastanet, Jacqueline ; Zhu, Jieping
Published in Journal of the American Chemical Society
Volume 124
Issue 4
Pages 583-590
Date 2002
ISSN 0002-7863
Keywords
Protective groups (N-terminal; importance of; in; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Substitution reaction (SNAr; intramol.; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Amino acids Role: RCT (Reactant); RACT (Reactant or reagent) (convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Peptides Role: SPN (Synthetic preparation); PREP (Preparation) (cyclic; alkaloidal; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Etherification (cycloetherification; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Alkaloids Role: SPN (Synthetic preparation); PREP (Preparation) (cyclopeptidyl; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Peptides Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (linear; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Cyclophanes Role: SPN (Synthetic preparation); PREP (Preparation) (polypeptide-tethered; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); sanjoinine G1 cyclopeptide alkaloid convergent synthesis; cyclophane polypeptide tethered convergent synthesis; nitrogen protective group terminal cyclopeptide alkaloid convergent synthesis; endocyclic aryl alkyl ether bond formation cyclopeptide alkaloid synthesis; cycloetherification SNAr reaction cyclopeptide alkaloid convergent synthesis
Note CAN 136:216920
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
402821-46-9P Role: BYP (Byproduct), PREP (Preparation) (convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); 10233-81-5P; 19526-09-1P (Sanjoinine A); 51059-42-8P (Zizyphine A); 107494-19-9P (Sanjoinine A) Role: PNU (Preparation, unclassified), PREP (Preparation) (convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); 1493-27-2 (1-Fluoro-2-nitrobenzene); 10148-70-6 ((2S,3S)-3-Hydroxyleucine); 13139-15-6; 13734-34-4 (N-Boc-L-Phenylalanine); 17469-89-5 (N,N-Dimethyl-L-phenylalanine); 56613-80-0 ((R)-Phenylglycinol); 90181-25-2; 93527-55-0; 157662-78-7 (4-Fluoro-3-nitrophenethylamine); 185393-96-8; 202478-35-1; 204264-64-2; 221004-71-3; 309714-45-2; 313055-06-0; 402725-86-4; 402725-87-5; 402824-42-4 Role: RCT (Reactant), RACT (Reactant or reagent) (convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); 185393-97-9P; 185393-98-0P; 185394-01-8P; 185394-02-9P; 185394-03-0P; 185418-75-1P; 185529-05-9P; 202120-60-3P; 202120-61-4P; 202134-18-7P; 202134-19-8P; 202217-48-9P; 202217-49-0P; 221004-69-9P; 221004-70-2P; 221004-75-7P; 221004-76-8P; 402725-88-6P; 402725-89-7P; 402821-43-6P; 402821-47-0P; 402822-31-5P; 402822-32-6P; 402822-33-7P; 402822-35-9P; 402822-36-0P; 402822-38-2P; 402822-39-3P; 402822-40-6P; 402822-41-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); 107462-36-2P ((-)-Sanjoinine G1); 185393-94-6P; 185393-95-7P; 185393-99-1P; 202120-54-5P; 221004-72-4P; 309714-47-4P; 402725-83-1P; 402725-84-2P; 402725-85-3P; 402821-44-7P; 402821-45-8P; 402822-34-8P; 402822-37-1P; 402822-42-8P Role: SPN (Synthetic preparation), PREP (Preparation) (convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification)
DOI https://doi.org/10.1021/ja0170807
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
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Published
Record creation date 2010-11-25