Shimizu Takeshi, Satoh Tomoharu, Murakoshi Katsunori, Sodeoka Mikiko
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan.
Org Lett. 2005 Dec 8;7(25):5573-6. doi: 10.1021/ol052039k.
[chemical reaction: see text]. The stereocontrolled total synthesis of (-)-spirofungin A (1) and (+)-spirofungin B (2a), polyketide-type antibiotics having various antifungal activities, has been achieved employing the Weinreb amide 8, the alkyne 9, and the vinyl boronate 5 readily available from the common intermediate 10. The first synthesis proceeded with a longest linear sequence of 31 steps, affording (-)-1 and (+)-2a in 7.9% and 5.2% overall yields, respectively.
[化学反应：见正文]。利用从常见中间体10容易获得的Weinreb酰胺8、炔烃9和乙烯基硼酸酯5，实现了具有多种抗真菌活性的聚酮类抗生素（-）-螺旋菌素A（1）和（+）-螺旋菌素B（2a）的立体控制全合成。首次合成的最长线性序列为31步，（-）-1和（+）-2a的总产率分别为7.9%和5.2%。
