Temal-Laieb, TaouesChastanet, JacquelineZhu, Jieping2010-11-252010-11-252010-11-25200210.1021/ja0170807https://infoscience.epfl.ch/handle/20.500.14299/58498A 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)]Protective groups (N-terminalimportance ofin; convergent approach to the total synthesis of the cyclopeptide alkaloid sanjoinine G1 via an SNAr cycloetherification); Substitution reaction (SNArintramol.; 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) (cyclicalkaloidal; 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 synthesisA Convergent Approach to Cyclopeptide Alkaloids: Total Synthesis of Sanjoinine G1text::journal::journal article::research article