Asymmetric total synthesis of (-)-spirofungin A and (+)-spirofungin B.
[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.
Shimizu
Takeshi
T
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. tshimizu@riken.jp
Satoh
Tomoharu
T
Murakoshi
Katsunori
K
Sodeoka
Mikiko
M
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000935:Antifungal Agents; D011714:Pyrans; D013141:Spiro Compounds; C114877:spirofungin A; C493365:spirofungin B