| Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Outline of Final Research Achievements |
The chemical synthesis of organohalogens has become a focal point of intensive studies in organic synthesis. In the present study, we established a synthetic route to napyradiomycin A1, a chlorinated antibiotic isolated from the culture broth of Chainia rubra MG802-AF1. Extensive screening of amine ligands in combination with Willgerodt reagent (PhICl2) led to the development of a C2-symmetric catalyst applicable to asymmetric dichlorination of allylic alcohols. We have also found that an enantioenriched dichloride is produced from a dehydro-α-lapachone derivative in some, albeit small, degree of asymmetric induction under the Nicolaou conditions using (DHQD)2PHAL-PhICl2, paving the way to asymmetric synthesis of the natural antibiotic. In addition, biological evaluation of the synthetic intermediates has culminated in the discovery of a new analogue useful for further medicinal studies.
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