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Synthesis of (−)-halichonic acid and (−)-halichonic acid B

Keith P. Reber and Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635. https://doi.org/10.3762/bjoc.18.174

Supporting Information

The supporting information file contains detailed experimental procedures, full characterization data and copies of ¹H and ¹³C NMR spectra for all new compounds, and complete NMR spectral assignments for compound (−)-1, (−)-2, 8, 9, 10, and 11. A tabular comparison between the NMR data reported for natural products (+)-1 and (+)-2 and that obtained for their synthetic enantiomers (−)-1 and (−)-2 is also provided.

Supporting Information File 1: Experimental procedures, characterization data and copies of ¹H and ¹³C NMR spectra.
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Synthesis of (−)-halichonic acid and (−)-halichonic acid B

Keith P. Reber and Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635. https://doi.org/10.3762/bjoc.18.174

How to Cite

Reber, K. P.; Niner, E. L. Beilstein J. Org. Chem. 2022, 18, 1629–1635. doi:10.3762/bjoc.18.174

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TY  - JOUR
A1  - Reber, Keith P.
A1  - Niner, Emma L.
T1  - Synthesis of (−)-halichonic acid and (−)-halichonic acid B
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 1629
EP  - 1635
SN  - 1860-5397
DO  - 10.3762/bjoc.18.174
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.174
KW  - alkaloid
KW  - amino acid
KW  - aza-Prins reaction
KW  - cascade reaction
KW  - natural product
N2  - 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.
ER  -

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Scholarly Works

Gouault, N.; Roydor, M.; Renault, J.; Banik, S.; Subba Reddy, B. V.; Lalli, C. One‐Pot Double Cyclizations Involving an Aza‐Prins Process. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202400617
Carroll, A. R.; Copp, B. R.; Grkovic, T.; Keyzers, R. A.; Prinsep, M. R. Marine natural products. Natural product reports 2024, 41, 162–207. doi:10.1039/d3np00061c

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