ORGN 428 |
| Young-Ger Suh, Seung-Yong Seo, Seung-Mann Paek, and Kwang-Ok Lee. Department of Pharmaceutical Chemistry, College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Kwanak-Gu, Seoul, 151-742, South Korea |
| Bacillariolide III was isolated from the culture medium of the marine diatom, Pseudonitzschia multiseries, a causative organism of amnesic shellfish poisoning by Shimizu et al. This extracellular metabolite features bicyclic system of hydroxycyclopentane and (Z)-pentenoic acid-bearing lactone ring. Bacillariolide I is known to possess significant inhibitory activity against phospholipase A2, but the biological function of bacillariolide III is still under investigation. The unique structural feature as well as the promising biological activity led us to the total synthesis of bacillariolide III. The total synthesis of bacillariolide III has been accomplished via 15 linear steps in a 14.6% overall yield from the known (R)-α-hydroxybutyrolactone. The key parts of this approach include the stereoselective construction of the cis-disubstituted hydroxycyclopentane skeleton employing Pd-catalyzed allylation and the convergent and stereocontrolled introduction of the (Z)-pentenoic acid using the ring-closing metathesis (RCM). |
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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
Division of Organic Chemistry |