Asymmetric Total Syntheses of (-)-Renieramycin M and G and (-)-Jorumycin Using Aziridine as a Lynchpin

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)]


Published in:
Organic Letters, 11, 23, 5558-5561
Year:
2009
Keywords:
Note:
CAN 152:12534
31-5
Alkaloids
CNRS, Centre de Recherche de Gif,Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
1523-7060
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)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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