3_11_05 - Massachusetts Institute of Technology Organic...

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Massachusetts Institute of Technology Organic Chemistry 5.512 March 11, 2005 Prof. Rick L. Danheiser Strategies for Stereocontrolled Synthesis O CO 2 H OH OH CO 2 H OH HO Prostaglandin A 2 G. Stork and S. Raucher J. Am. Chem. Soc. 1976 , 98, 1583 G. Stork, T. Takahashi, I. Kawamoto, and T. Suzuki 1978 , 100 , 8272 Case Study #2 5 6 8 9 11 12 15 13 14 Prostaglandin F α Total Synthesis of Prostaglandins A Sweet Approach References For discussions of the use of chiral natural products as starting materials for the synthesis of complex molecules, see (1) S. Hanessian "Total Synthesis of Natural Products: The 'Chiron Approach' ", Pergamon Press: Oxford, 1983. (2) T.-L. Ho "Enantioselective Synthesis: Natural Products from Chiral Terpenes", Wiley Interscience: New York, 1992.
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O O O HO OH MeO 2 C O O O (MeO) 3 C CO 2 Me Am CO 2 H O OEt O C CO 2 Me N HCl-MeOH-Et 2 O -20° 14 d; MeOH-pent 25° 4 d OCO 2 Me OH OH MeO 2 C OH OH O O HO MeO 2 C OH H MeO 2 C CO 2 Me H OH OCO
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3_11_05 - Massachusetts Institute of Technology Organic...

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