Mandal Amit K, Schneekloth John S, Crews Craig M
Department of Chemistry, Yale University, New Haven, CT 06520-8103, USA.
Org Lett. 2005 Aug 18;7(17):3645-8. doi: 10.1021/ol051175m.
The preparation of three fragments for the total synthesis of amphidinolide B1 has been described. The C16 stereochemistry was set by asymmetric allylic alkylation. C21 and C25 stereogenic centers were set by an enantioselective/diastereoselective double allylation reaction. The C9 configuration was set by an asymmetric heteroene reaction. A differentially substituted stereodefined 1,3-diene iodide was synthesized by iodide-mediated S(N)2' reaction. A novel stereoselective method to assemble a 1,3-diene by coupling an allenic acetate and (B)-alkylborane is also reported. [structure: see text]
已报道了用于两性霉素B1全合成的三个片段的制备。C16立体化学通过不对称烯丙基烷基化确定。C21和C25立体中心通过对映选择性/非对映选择性双烯丙基化反应确定。C9构型通过不对称杂烯反应确定。通过碘介导的S(N)2'反应合成了一种差异取代的立体定义的1,3-二烯碘化物。还报道了一种通过将烯丙基乙酸酯和(B)-烷基硼烷偶联来组装1,3-二烯的新型立体选择性方法。[结构：见正文]
