Liang Bo, Negishi Ei-ichi
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Org Lett. 2008 Jan 17;10(2):193-5. doi: 10.1021/ol702272d. Epub 2007 Dec 13.
ZACA-lipase-catalyzed acetylation tandem process has been shown to proceed satisfactorily with either TBS-protected 4-penten-1-ol or 3-buten-1-ol to provide the corresponding enantiomerically pure (R)-2-ethyl-1-alkanols. Either (R)-5 or (R)-6 was converted to 3 in seven steps. The other fragment 4 was synthesized in nine steps from (-)-(S)-citronellol. Conversion of 3 and 4 into 99% pure fluvirucinine A1 was achieved in four steps via amidation-ring closing metathesis, the overall yield in the longest linear sequence being 34% (13 steps).
ZACA脂肪酶催化的乙酰化串联过程已被证明，无论是对叔丁基二甲基硅烷基（TBS）保护的4-戊烯-1-醇还是3-丁烯-1-醇，该过程都能顺利进行，以提供相应的对映体纯的（R）-2-乙基-1-链烷醇。（R）-5或（R）-6均可通过七步反应转化为3。另一个片段4由（-）-（S）-香茅醇经九步合成。通过酰胺化-闭环复分解反应，经四步反应将3和4转化为纯度为99%的氟鲁辛宁A1，最长线性序列的总收率为34%（13步）。
