Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
Org Lett. 2012 Jan 6;14(1):426-8. doi: 10.1021/ol203161u. Epub 2011 Dec 7.
Tirandamycin C is a newly isolated member of the tetramic acid family natural products. We described herein the first enantioselective synthesis of natural (-)-tirandamycin C, the postulated biosynthetic precursor of other members of this family. The highly stereoselective (>15:1) mismatched double asymmetric γ-stannylcrotylboration reaction of aldehyde 8 with crotylborane reagent (R)-E-9 was utilized to access the key anti,anti-stereotriad 18.
替拉霉素 C 是一个新分离的四氢酸家族天然产物成员。本文描述了天然(-)-替拉霉素 C 的首次对映选择性合成,该化合物是该家族其他成员的假定生物合成前体。通过高度立体选择性 (>15:1) 的非匹配双不对称γ-锡基烯丙基硼化反应,将醛 8 与烯丙基硼试剂 (R)-E-9 反应,得到关键的反式,反式立体三嗪 18。