Synthesis of the C16-C28 spiroketal subunit of spongistatin 1 (altohyrtin A): The pyrone approach

被引:37
作者
Crimmins, MT [1 ]
Katz, JD [1 ]
机构
[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/ol005605e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The synthesis of the CD spiroketal fragment of spongistatin 1 (altohyrtin A) has been accomplished utilizing the addition of a metalated pyrone to an aldehyde and subsequent acid-catalyzed spirocyclization. A stereoselective hydrogenation and subsequent conformational inversion establish the C19 stereocenter and the axial-equatorial spiroketal center.
引用
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页码:957 / 960
页数:4
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