Synthesis of fully functionalized aglycone of lycoperdinoside A and BElectronic supplementary information (ESI) available: The copies of 1H and 13C NMR spectra for compounds 13-19, 7, 20-28, 9, 6, 29 and 30. See DOI: 10.1039/c4ob01716a

This article reported the synthesis of fully functionalized aglycone of lycoperdinoside A and B. Pd-catalyzed Stille-Migita cross coupling between E -vinyl iodide 6 and E -vinyl stannane 23 established the highly substituted E , E -diene unit present in lycoperdinoside A and B. The other two Z -olef...

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Main Authors: Chandrasekhar, Balla, Athe, Sudhakar, Reddy, P. Purushotham, Ghosh, Subhash
Format: Article
Language:English
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Summary:This article reported the synthesis of fully functionalized aglycone of lycoperdinoside A and B. Pd-catalyzed Stille-Migita cross coupling between E -vinyl iodide 6 and E -vinyl stannane 23 established the highly substituted E , E -diene unit present in lycoperdinoside A and B. The other two Z -olefins present in the molecule were introduced by means of cis -selective Horner-Wadsworth-Emmons reaction with Still-Gennari phosphonate. Evans syn - and anti -aldol reactions were utilized to fix six of the seven stereo centres present in the aglycone. Synthesis of fully functionalized aglycone of lycoperdinoside A and B is achieved via Pd-catalyzed Stille-Migita cross coupling and Evans syn - and anti aldol reactions as key steps.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01716a