Synthesis of Several Cleistrioside and Cleistetroside Natural Products via a Divergent De Novo Asymmetric Approach

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• 作者：Bulan Wu ; Miaosheng Li ; George A. O&#8217 ; Doherty
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：December 3, 2010
• 年：2010
• 卷：12
• 期：23
• 页码：5466-5469
• 全文大小：320K
• 年卷期：v.12,no.23(December 3, 2010)
• ISSN：1523-7052

文摘

The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19−24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective palladium-catalyzed glycosylation, ketone reduction and dihydroxylation.