Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 18, Issue -, Pages 1629-1635Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.18.174
Keywords
alkaloid; amino acid; aza-Prins reaction; cascade reaction; natural product
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Funding
- Fisher College of Science and Mathematics (Towson University)
- instrumentation provided through the National Science Foundation [0923051, 1531562]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0923051, 1531562] Funding Source: National Science Foundation
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The synthesis of amino acids (-)-halichonic acid and (-)-halichonic acid B has been successfully achieved in ten steps starting from commercially available (-)-alpha-bisabolol. A new purification method involving recrystallization of the benzamide derivative of (-)-7-amino-7,8-dihydrobisabolene has been developed to obtain enantiomerically pure form. The key intramolecular aza-Prins reaction formed the characteristic ring system of halichonic acid and halichonic acid B in a specific ratio.
The first syntheses of the amino acids (-)-halichonic acid and (-)-halichonic acid B have been achieved in ten steps starting from commercially available (-)-alpha-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 intramolecu-lar 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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