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Published on: February 7, 2019
Asymmetric total synthesis of (-)-spirofungin A and (+)-spirofungin B
Takeshi Shimizu1, Tomoharu Satoh, Katsunori Murakoshi
1RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. tshimizu@riken.jp
Abstract:
[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.
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