Formal total syntheses of the (-)-salicylihalamides A and B from D-glucose and L-rhamnose

Torsten Haack, Kyounglang Haack, Wibke E. Diederich, Burchelle Blackman, Subho Roy, Srinivas Pusuluri, Gunda I. Georg

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Two formal total syntheses of the (-)-salicylihalamides, based on chiral pool approaches, are reported. D-Glucose and L-rhamnose were used to prepare advanced intermediates 23 and 54, which can be converted in three or four steps, respectively, to the target compounds. The synthesis of 23 from a known D-glucose-derivative was accomplished in 12 steps and 17% overall yield, and the synthesis of 54 from a known L-rhamnose-derivative was done in nine steps and 6% overall yield. A key step in the synthesis was a ring-closing metathesis reaction to prepare the macrocyclic ring system. It was demonstrated that the phenolic protecting group was critical for inducing the preferential formation of the desired E isomer. It was further shown that the protecting group at the CIS hydroxyl group had no significant influence on the E:Z ratio during the ring-closing metathesis reaction.

Original languageEnglish (US)
Pages (from-to)7592-7604
Number of pages13
JournalJournal of Organic Chemistry
Volume70
Issue number19
DOIs
StatePublished - Sep 16 2005

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