Enantioselective synthesis of a mitosane core assisted by diversity-based catalyst discovery

Authors
Papaioannou, N Evans, CA Blank, JT Miller, SJ
Citation
N. Papaioannou et al., Enantioselective synthesis of a mitosane core assisted by diversity-based catalyst discovery, ORG LETT, 3(18), 2001, pp. 2879-2882
Citations number
40
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
18
Year of publication
2001
Pages
2879 - 2882
Database
ISI
SICI code
1523-7060(20010906)3:18<2879:ESOAMC>2.0.ZU;2-R
Abstract
[GRAPHICS] Synthesis of mitosane 1 in optically pure form is reported. A retrosyntheti c plan that proceeds through racemic allylic alcohol 3 was carried out. Thi s intermediate served as a test substrate for a rapid screen of a small lib rary (152 members) of peptide-based kinetic resolution catalysts. Peptide 9 was found to effect kinetic resolution with k(rel) = 27.Alcohol (-)-3 was then converted to optically pure (-)-1 in eight steps.