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Novel "protecting group-dependent" alkylation-RCM strategy to medium-sized oxacycles: First total synthesis of (-)-isoprelaurefucin
- Issue Date
- Oct-2005
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.70, no.22, pp 8723 - 8729
- Pages
- 7
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 70
- Number
- 22
- Start Page
- 8723
- End Page
- 8729
- ISSN
- 0022-3263
1520-6904
- Abstract
- [GRAPHICS] A novel "protecting group-dependent" alkylation strategy was developed for complementary diastereoselective syntheses of alpha,alpha'-syn- and alpha,alpha'-anti-bis-alkenes 2 and 3, which represent ring-closing metathesis (RCM) substrates for medium-sized oxacycles. This principle has been applied to a stereoselective and concise total synthesis of (-)-isoprelaurefucin (4) in 14 steps in 12% overall yield from known epoxide 8.
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