有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
6,6-スピロケタール天然物reveromycin A,Bおよびspirofungin A,Bの合成と活性
清水 猛
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ジャーナル 認証あり

2009 年 67 巻 1 号 p. 51-64

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The first asymmetric total synthesis of reveromycin A (1), a potent inhibitor of isoleucyl tRNA synthetase, has been accomplished based on the stereocontrolled construction of the 6,6-spiroketal system, efficient succinylation of the tert-alcohol under high pressure as a key step. The stereocontrolled total synthesis of (−)-spirofungin A (5) and (+)-spirofungin B (6a), polyketide-type antibiotics having various antifungal activities, has been achieved employing the Weinreb amide, the alkyne and the vinyl boronate readily available from the common intermediate employing Horner-Emmons reaction and Suzuki coupling reaction for the construction of the both side chains. The succinates of the tertiary hydroxyl group having the formyl group in the structures were conveniently synthesized by oxidative cleavage of the dihydropyrans prepared from the lactone via coupling of the ketene acetal triflates and zinc homoenolate. Various derivatives of 1, 5 and 6a were synthesized and their inhibitory effects on both the isoleucyl-tRNA synthetase activity and the survival of osteoclasts, and activities on the morphological reversion of srcts-NRK cells were examined.

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© 2009 社団法人 有機合成化学協会
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