Enantioselective Synthesis of an Aziridinomitosane and Selective Functionalizations of a Key Intermediate

• Published in: Journal of organic chemistry Vol. 68; no. 7; pp. 2728 - 2734
• Main Authors: Papaioannou, Nikolaos, Blank, Jarred T, Miller, Scott J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.04.2003; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Chemistry, Organic - methods; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Indicators and Reagents; Isatin - chemistry; Mitomycin - chemical synthesis; Mitomycin - chemistry; Mitomycins; Molecular Structure; Organic chemistry; Peptides - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; ENANTIOMERIC PAIR; ALCOHOLS; METHOXY-N-METHYLAMIDES; FR900482; RING-CLOSING METATHESIS; KINETIC RESOLUTION; MITOMYCIN-C; OLEFIN METATHESIS; COMPLETION; CATALYSTS; Cyclization; Enantioselectivity; Nitrogen heterocycle; Metathesis; Bicyclic compound; Alcohol; Aziridine derivatives; Tetracyclic compound; Oxygen heterocycle; Chemical synthesis; Ketone

An enantioselective synthesis of mitosane core (−)-1 has been achieved. Key steps include a rapid assembly of a key eight-membered-ring intermediate employing ring-closing metathesis. Kinetic resolution of an advanced secondary alcohol was then accomplished by using a peptide-based asymmetric acyl t...