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Spongistatin synthetic studies. 1. Construction of a C(29–48) subtarget

✍ Scribed by Amos B. Smith III; Linghang Zhuang; Christopher S. Brook; Armen M. Boldi; Mark D. McBriar; William H. Moser; Noriaki Murase; Kiyoshi Nakayama; Patrick R. Verhoest; Qiyan Lin


Book ID
108386391
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
270 KB
Volume
38
Category
Article
ISSN
0040-4039

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A convergent synthesis of the C(1-17) AB-ring subunit of the spongistatins, exceedingly scarce and highly ant]mitotic polyether macrolides, has been achieved via a one-flask dithiane bisalkylation, stereocontrolled spiroketalization, and Julia sulfone coupling/methylenation. © ]997 Elsevier Science

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A convergent synthesis of the C29-C44 fragment, the common subunit of the spongipyran macrolides is described. The key step of the synthesis is the C-glycosidation reaction which is based on coupling of the lithiated F-ring sulfone with the E-ring aldehyde, and subsequent reductive desulfonylation t