a general and simple diastereoselective reduction by l-selectride efficient synthesis of protected (4s,5s)-dihydroxy amides一般简单的diastereoselective减少l-selectride高效合成的保护(4,5 s)二羟酰胺.pdfVIP

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a general and simple diastereoselective reduction by l-selectride efficient synthesis of protected (4s,5s)-dihydroxy amides一般简单的diastereoselective减少l-selectride高效合成的保护(4,5 s)二羟酰胺.pdf

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a general and simple diastereoselective reduction by l-selectride efficient synthesis of protected (4s,5s)-dihydroxy amides一般简单的diastereoselective减少l-selectride高效合成的保护(4,5 s)二羟酰胺

Molecules 2010, 15, 2771-2781; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides Bo Yin, Dong-Nai Ye, Kai-Hui Yu and Liang-Xian Liu * Department of Chemistry and Biology, Ganan Normal University, Ganzhou, Jiangxi 341000, China * Author to whom correspondence should be addressed; E-Mail: lxliu@; Tel: +86-797- 8397630; Fax: +86-797-8393670. Received: 18 December 2009; in revised form: 24 March 2010 / Accepted: 12 April 2010 / Published: 16 April 2010 Abstract: A general approach to (4S,5S)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl) amides 10 based on a diastereoselective reduction of (5S,6RS)-6-alkyl-5-benzyloxy-6- hydroxy-2-piperidinones 6 and their tautomeric ring-opened keto amides 7 is described. The reduction with L-Selectride at -20 °C to room temperature afforded the products 10 in excellent yields and moderate to high syn-diastereoselectivities. Keywords: L-Selectride; 3-hydroxyglutarimide; (4S,5S)-dihydroxyamide 1. Introduction The (4,5)-dihydroxycarboxylate moiety is a critical framework shared by many bioactive compounds, such as Microcarpalide (1), which is a 10-membered lactone that was isolated from the fermentation broth of an unidentified endophytic fungus by Hemscheidt and co-workers in 2001 [1], and Kalanchosine dimalate (KMC, 2) [2], which is an anti-inflammatory salt from the fresh juice of the aerial parts of