Asymmetric Total Syntheses of (-)-Renieramycin M and G and (-)-Jorumycin Using Aziridine as a Lynchpin
2009
Résumé
Using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps, (-)-renieramycin M I [R = (Z)-MeCH:CMeCO; R = NC; R1 = H], (-)-renieramycin G I [R = (Z)-MeCH:CMeCO; RR1 = O], (-)-jorumycin I (R = MeCO; R1 = HO; R2 = H), and (-)-jorunnamycin A I (R = H; R1 = NC; R2 = H) are prepd. convergently. [on SciFinder (R)]
Détails
Titre
Asymmetric Total Syntheses of (-)-Renieramycin M and G and (-)-Jorumycin Using Aziridine as a Lynchpin
Auteur(s)
Wu, Yan-Chao ; Zhu, Jieping
Publié dans
Organic Letters
Volume
11
Numéro
23
Pages
5558-5561
Date
2009
ISSN
1523-7060
Mots-clés (libres)
Heterocyclic compounds Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (nitrogen; aziridines; stereoselective prepn. of (-)-renieramycins G and M; (-)-jorumycin; and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); Stereoselective synthesis (stereoselective prepn. of (-)-renieramycins G and M; (-)-jorumycin; and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); Pictet-Spengler cyclocondensation reaction; Ring opening (stereoselective; stereoselective prepn. of (-)-renieramycins G and M; (-)-jorumycin; and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); renieramycin G M stereoselective nonracemic prepn; jorumycin stereoselective nonracemic prepn; jorunnamycin A stereoselective nonracemic prepn; ring opening reaction amino acid derived aziridine prepn renieramycin; Pictet Spengler reaction amino acid derived aziridine prepn renieramycin
Note
CAN 152:12534
31-5
Alkaloids
CNRS, Centre de Recherche de Gif,Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
64-19-7 (Acetic acid); 1707-03-5 (Diphenylphosphinic acid) Role: CAT (Catalyst use), USES (Uses) (optimized cocatalyst for Pictet-Spengler reaction of a nonracemic amino acid-derived aziridinecarboxaldehyde used as a key step in stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A); 1907-33-1; 4465-44-5 (N-Trityl-L-serine methyl ester) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of nonracemic amino acid-derived aziridines and their use as building blocks in stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A); 75154-68-6P; 126496-79-5P; 152706-23-5P; 178602-42-1P; 1171118-67-4P; 1198080-11-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of nonracemic amino acid-derived aziridines and their use as building blocks in stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A); 565-63-9 (Angelic acid); 5673-07-4 (1,3-Dimethoxy-2-methylbenzene); 60656-87-3 (Benzyloxyacetaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); 7149-92-0P (2,4-Dimethoxy-3-methylbenzaldehyde); 19676-67-6P (2,4-Dimethoxy-3-methylphenol); 185981-74-2P; 185981-82-2P; 701911-92-4P ((-)-Jorunnamycin A); 701911-94-6P (Cyanojorumycin); 866110-94-3P; 866110-95-4P; 1124171-91-0P; 1198080-12-4P; 1198080-13-5P; 1198080-14-6P; 1198080-15-7P; 1198080-16-8P; 1198080-17-9P; 1198080-18-0P; 1198080-19-1P; 1198080-20-4P; 1198080-21-5P; 1198080-22-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); 143458-75-7P ((-)-Renieramycin G); 304852-37-7P ((-)-Jorumycin); 631913-64-9P ((-)-Renieramycin M) Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps)
31-5
Alkaloids
CNRS, Centre de Recherche de Gif,Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
64-19-7 (Acetic acid); 1707-03-5 (Diphenylphosphinic acid) Role: CAT (Catalyst use), USES (Uses) (optimized cocatalyst for Pictet-Spengler reaction of a nonracemic amino acid-derived aziridinecarboxaldehyde used as a key step in stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A); 1907-33-1; 4465-44-5 (N-Trityl-L-serine methyl ester) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of nonracemic amino acid-derived aziridines and their use as building blocks in stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A); 75154-68-6P; 126496-79-5P; 152706-23-5P; 178602-42-1P; 1171118-67-4P; 1198080-11-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of nonracemic amino acid-derived aziridines and their use as building blocks in stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A); 565-63-9 (Angelic acid); 5673-07-4 (1,3-Dimethoxy-2-methylbenzene); 60656-87-3 (Benzyloxyacetaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); 7149-92-0P (2,4-Dimethoxy-3-methylbenzaldehyde); 19676-67-6P (2,4-Dimethoxy-3-methylphenol); 185981-74-2P; 185981-82-2P; 701911-92-4P ((-)-Jorunnamycin A); 701911-94-6P (Cyanojorumycin); 866110-94-3P; 866110-95-4P; 1124171-91-0P; 1198080-12-4P; 1198080-13-5P; 1198080-14-6P; 1198080-15-7P; 1198080-16-8P; 1198080-17-9P; 1198080-18-0P; 1198080-19-1P; 1198080-20-4P; 1198080-21-5P; 1198080-22-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps); 143458-75-7P ((-)-Renieramycin G); 304852-37-7P ((-)-Jorumycin); 631913-64-9P ((-)-Renieramycin M) Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of (-)-renieramycins G and M, (-)-jorumycin, and (-)-jorunnamycin A using ring opening and Pictet-Spengler reactions of nonracemic amino acid-derived aziridine building blocks as key steps)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2010-11-25