Spongistatin synthetic studies. 2. Assembly of the C(18–28) spiroketal

Amos B. Smith; Linghang Zhuang; Christopher S. Brook; Qiyan Lin; William H. Moser; Robert E. Lee Trout; Armen M. Boldi

doi:10.1016/s0040-4039(97)10500-7

Spongistatin synthetic studies. 2. Assembly of the C(18–28) spiroketal

Amos B. Smith(Monell Chemical Senses Center), Linghang Zhuang(Monell Chemical Senses Center), Christopher S. Brook(Monell Chemical Senses Center), Qiyan Lin(Monell Chemical Senses Center), William H. Moser(Monell Chemical Senses Center), Robert E. Lee Trout(Monell Chemical Senses Center), Armen M. Boldi(Monell Chemical Senses Center)

Tetrahedron Letters

December 1, 1997

10.1016/s0040-4039(97)10500-7

Cited by 52Open Access

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Abstract

The C(18–28) CD-ring spiroketal subunit of the spongistatins, marine polyether macrolides with unprecedented antitumor activity, has been generated via a highly convergent and completely stereocontrolled sequence. Key operations include a one-flask dithiane bisalkylation and a metal-assisted spiroketal equilibration.

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