Halim Rosliana, Brimble Margaret A, Merten Jörn
Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Org Lett. 2005 Jun 23;7(13):2659-62. doi: 10.1021/ol0507975.
[reaction: see text] A highly stereocontrolled synthesis of the C1-C16 ABC spiroacetal-containing fragment 5 of PTX7 (4) has been achieved. Appendage of the C ring to the AB fragment involved Wittig reaction of spiroacetal aldehyde 8 with a stabilized ylide 9 followed by displacement of allylic iodide 27 with a lithium acetylide to afford enyne 7. Fructose-derived chiral dioxirane and dihydroxylation were then used to introduce the correct functionality in the tetrahydrofuran C ring.
[反应：见正文] 已实现了对紫杉醇7（4）中含C1-C16 ABC螺缩醛片段5的高度立体控制合成。将C环连接到AB片段涉及螺缩醛醛8与稳定叶立德9的维蒂希反应，随后用乙炔锂取代烯丙基碘27以得到烯炔7。然后使用果糖衍生的手性二氧杂环丙烷和二羟基化反应在四氢呋喃C环中引入正确的官能团。
