sg_vi - Massachusetts Institute of Technology 5.13 Organic...

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Unformatted text preview: Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003 Outline & Study Guide for Unit VI. Enols & Enolates O OH H 3 C CH 3 H 3 C CH 2 Keto Enol H 3 C CH 2 O H 3 C CH 2 O Enolate there is a great deal of interest in probing the specific OH mode of action of the spongistatins. The problem? Very little of the active compounds can be isolated CH 2 from the natural sources. In addition, although five HO Me different research groups had successfully synthesized a member of the spongistatin family by 2002, none of these syntheses generated more than four milligrams of the final product! OMe To overcome this problem, Professor Clayton Figure 1 spongistatin 2 (altohyrtin C) = Bond Formed Using Enolate Chemistry Heathcock at the University of California, Berkeley set out to develop a synthesis that could generate multi-gram quantities of spongistatin 2. His final In 1993 and 1994, a family of marine-derived natural products were isolated from three different sea sponges. Several of these natural products, including spongistatin 2 three different sea sponges....
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sg_vi - Massachusetts Institute of Technology 5.13 Organic...

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