Yuan Zhong Qing, Ishikawa Hayato, Boger Dale L
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Org Lett. 2005 Feb 17;7(4):741-4. doi: 10.1021/ol050017s.
Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation. [Reaction: see text]
详细介绍了阿西多斯佩尔马生物碱4-去乙酰氧基-6,7-二氢长春多灵(12)和米诺文(1)两种对映体的高效且异常简洁的全合成。1,3,4-恶二唑8的分子内串联狄尔斯-阿尔德/1,3-偶极环加成反应是该序列中的关键步骤,此反应形成了三个新环、四个新的碳-碳键和五个立体中心。光学活性物质的可得性使得对米诺文的对映体纯度及其报道的异常旋光度来源进行了评估。[反应:见正文]