ORGN 433 |
Progress toward the total synthesis of yokonolide A
| Michael T. Crimmins and Aaron C. Smith. Department of Chemistry, University of North Carolina at Chapel Hill, Venable and Kenan Laboratories of Chemistry, CB# 3290, Chapel Hill, NC 27599 |
Yokonolide A is a novel 22-membered spiroketal-macrolide isolated from Streptomyces diastatochromogenes B59. It is an inhibitor of signal transduction in certain plant hormones. Our approach to the synthesis of yokonolide A includes an asymmetric aldol addition with N-acetyl-thiazolidinethione to install the C29 stereocenter. Cross metathesis and subsequent hydrogenation form the C24-C25 carbon-carbon bond. Aldol additions with N-propionyl-thiazolidinethione construct the stereocenters at C6, C7, C19, and C20. Other key steps include spiroketalization and ring-closing metathesis at C14-C15 to complete the macrolactone core. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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