Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin鈥揕ee CsF/CuI sp3鈥搒p2-Stille Cross-Coupling. Confirmation of the Cre

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• 作者：Liping Wang ; Karl J. Hale
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：17
• 期：17
• 页码：4200-4203
• 全文大小：371K
• ISSN：1523-7052

文摘

A convenient asymmetric total synthesis of the potent HIF-1 inhibitory antitumor natural product, (鈭?- or (+)-(8R)-mycothiazole (1), is described. Not only does our synthesis confirm the 2006 structural reassignment made by Crews (Crews, P., et al. J. Nat. Prod. 2006, 69, 145), it revises the [伪]_D data previously reported for this molecule in MeOH from 鈭?3.7掳 to +42.3掳. The newly developed route to (8R)-1 sets the C(8)鈥揙H stereocenter via Sharpless AE/2,3-epoxy alcohol reductive ring opening and utilizes two Baldwin鈥揕ee CsF/cat. CuI Stille cross-coupling reactions with vinylstannanes 8 and 3 to efficiently elaborate the C(1)鈥揅(4) and C(14)鈥揅(18) sectors.