Asymmetric Total Syntheses of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G

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• 作者：Jonathan W. Lane ; Yuyin Chen ; and Robert M. Williams
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：September 14, 2005
• 年：2005
• 卷：127
• 期：36
• 页码：12684 - 12690
• 全文大小：250K
• 年卷期：v.127,no.36(September 14, 2005)
• ISSN：1520-5126

文摘

The total synthesis of (-)-jorumycin (1) and (-)-renieramycin G (2) has been accomplished in25 and 23 steps, respectively, from 5-benzyloxy-2,4-dimethoxy-3-methyl-benzyl alcohol. The synthesisfeatures a substrate-tunable stereoselective intramolecular Pictet-Spengler-type reaction for the constructionof the key pentacyclic core of both targets, bearing either the natural configuration or the epimericconfiguration at C-3. With access to a C-3 epi-pentacyclic framework, 3-epi-jorumycin (32) and 3-epi-renieramycin G (34) were also successfully synthesized. Furthermore, preliminary biological evaluation of3-epi-jorumycin (32), in addition to relevant synthetic intermediates, revealed that significant cytotoxicityhad been retained in these compounds. Therefore, these early studies constitute the basis for a new structureactivity relationship (SAR) investigation for this class of antitumor antibiotics.