Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as...

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Veröffentlicht in:Natural product communications 2018-07, Vol.13 (7)
Hauptverfasser: Chandrakanth, Dandekar, Rao, Yerragorla Gopala, Swamy, Tallapally, Biradar, Dhanraj O, Vishnupriya, Lonavath, Reddy, Basi V Subba
Format: Artikel
Sprache:eng
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Zusammenfassung:A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1801300721