埃坡菌素A和B的结构修正与合成
Structure revision and syntheses of epohelmins A and B.
作者信息
Snider Barry B, Gao Xiaolei
机构信息
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
出版信息
Org Lett. 2005 Sep 29;7(20):4419-22. doi: 10.1021/ol0516061.
[structures: see text] Epohelmins A (24) and B (26) have been reassigned as pyrrolizidin-1-ols, rather than the proposed 9-oxa-4-azabicyclo[6.1.0]nonane structures 1 and 2, respectively. Syntheses of epohelmin A (24) (eight steps, 52% overall yield) and epohelmin B (26) (11 steps, 43% overall yield) have been achieved starting from N-Cbz-(S)-prolinal (9) and ortho ester ketone 17 using a stereoselective aldol reaction and a stereoselective reductive cyclization as the key steps.
[结构：见正文] 埃坡霉素A（24）和B（26）已被重新归类为吡咯里西啶-1-醇，而不是之前提出的分别为9-氧杂-4-氮杂双环[6.1.0]壬烷结构1和2。以N-Cbz-(S)-脯氨醛（9）和原酸酯酮17为起始原料，通过立体选择性羟醛缩合反应和立体选择性还原环化反应作为关键步骤，已完成了埃坡霉素A（24）（八步，总收率52%）和埃坡霉素B（26）（十一步，总收率43%）的合成。
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