Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
Abstract: Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation‐borylation reaction to attach the cyclopropyl‐containing side chain.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A ; volume:128 ; number:7 ; year:2016 ; pages:2544-2548 ; extent:5
Angewandte Chemie ; 128, Heft 7 (2016), 2544-2548 (gesamt 5)
- Urheber
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Millán, Alba
Smith, James R.
Chen, Jack L.‐Y.
Aggarwal, Varinder K.
- DOI
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10.1002/ange.201511140
- URN
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urn:nbn:de:101:1-2022101007060862511334
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:32 MESZ
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Beteiligte
- Millán, Alba
- Smith, James R.
- Chen, Jack L.‐Y.
- Aggarwal, Varinder K.
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