ArticleBeilstein journal of organic chemistry2022
Synthesis of (-)-halichonic acid and (-)-halichonic acid B.
Article in Beilstein journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Marine Natural Products From Indonesia and Their Biosynthetic Origins: Part 1: Terpenoids and Meroterpenoids.Chemistry & biodiversity · 2026Review
- Total synthesis of natural products facilitated by prins reaction: a review.RSC advances · 2026Review
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2 authors.
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Abstract
The first syntheses of the amino acids (-)-halichonic acid and (-)-halichonic acid B have been achieved in ten steps starting from commercially available (-)-α-bisabolol. The optimized synthetic route includes a new purification method for isolating (-)-7-amino-7,8-dihydrobisabolene in enantiomerically pure form via recrystallization of its benzamide derivative. The key intramolecular aza-Prins reaction forms the characteristic 3-azabicyclo[3.3.1]nonane ring system of halichonic acid along with the lactonized form of halichonic acid B in an 8:1 ratio. Optical rotation measurements confirmed that these synthetic compounds were in fact the enantiomers of the natural products, establishing both the relative and absolute configurations of the halichonic acids.
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