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Unusual Epimerization in Styryllactones: Synthesis of (-)-5-Hydroxygoniothalamin, (-)-5-Acetylgoniothalamin, and O-TBS-Goniopypyrone.

ABSTRACT: (-)-5-Hydroxygoniothalamin, (-)-5-acetylgoniothalamin, and (+)-5-hydroxygoniothalamin, isolated from the Goniothalamus genus, are synthesized from triacetyl-O-d-glucal by employing the Ferrier reaction, Mitsunobu reaction, and Jones oxidation as key steps. The synthetic procedure also yields the epimers of (-)-5-hydroxygoniothalamin and (+)-5-hydroxygoniothalamin employing acid-mediated transition-metal-free epimerization at C-5 of styryllactones. Further studies reveal that the epimerization is facilitated by the phenyl group present on the styryllactones. Also, depending on the dihydroxylation reaction conditions, various analogues of saturated styryllactones are synthesized utilizing oxa-Michael reaction conditions.

SUBMITTER: Kotammagari TK 

PROVIDER: S-EPMC6941370 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Unusual Epimerization in Styryllactones: Synthesis of (-)-5-Hydroxygoniothalamin, (-)-5-Acetylgoniothalamin, and <i>O</i>-TBS-Goniopypyrone.

Kotammagari Tharun K TK   Paul Sayantan S   Bhattacharya Asish K AK  

ACS omega 20191217 27

(-)-5-Hydroxygoniothalamin, (-)-5-acetylgoniothalamin, and (+)-5-hydroxygoniothalamin, isolated from the <i>Goniothalamus</i> genus, are synthesized from triacetyl-<i>O</i>-d-glucal by employing the Ferrier reaction, Mitsunobu reaction, and Jones oxidation as key steps. The synthetic procedure also yields the epimers of (-)-5-hydroxygoniothalamin and (+)-5-hydroxygoniothalamin employing acid-mediated transition-metal-free epimerization at C-5 of styryllactones. Further studies reveal that the ep  ...[more]