Abstract
Cyclopentenyl carbinols are oxidatively cleaved and cyclized into a class of terpenylic acid analogues in the presence of oxone and sodium periodate in good yields.
Graphical abstract
References
Babar ZB, Ashraf F, Park J-H, Dao PDQ, Cho CS, Lim H-J (2020) Exploring volatility properties of discrete secondary organic aerosol constituents of α-pinene and polycyclic aromatic hydrocarbons. ACS Earth Space Chem 4:2299–2311. https://doi.org/10.1021/acsearthspacechem.0c00210
Claeys M, Iimuma Y, Szmigielski R, Surratt JD, Blockhuys F, Alsenoy CV, Böge O, Sierau B, Gómez-González Y, Vermeylen R, Veken PVD, Shahgholi M, Chan AWH, Herrmann H, Seinfeld JH, Maenhaut W (2009) Terpenylic acid and related compounds from the oxidation of α-pinene: implications for new particle formation and growth above forests. Environ Sci Technol 43:6976–6982. https://doi.org/10.1021/es9007596
Dao PDQ, Ho SL, Lim H-J, Cho CS (2018) Microwave-assisted cyclization under mildly basic conditions: synthesis of 6H-benzo[c]chromen-6-ones and their 7,8,9,10-tetrahydro analogues. J Org Chem 83:4140–4746. https://doi.org/10.1021/acs.joc.8b00048
Dryhurst G (1970) Periodate oxidation of diol and other functional groups. Analytical and structural applications. Pergamon, Oxford, chap 3, p 24
Garst JF, Soriaga MP (2004) Grignard reagent formation. Coord Chem Rev 248:623–652. https://doi.org/10.1016/j.ccr.2004.02.018
Guzmán A, Mendoza S, Diaz E (1981) 3,4-Disubstituted 4-alkanolides (butyrolactones) from 5,6-dihydro-2-pyrone. Synthesis 1981:989–991. https://doi.org/10.1055/s-1981-29673
Ho SL, Cho CS, Sohn H-S (2015a) Microwave-assisted copper-powder-catalyzed coupling and cyclization of β-bromo-α, β-unsaturated carboxylic acids with 1,3-diketones leading to 2H-pyran-2-ones. Synthesis 47:216–220. https://doi.org/10.1055/s-0034-1379103
Ho SL, Yoon IC, Cho CS, Choi H-J (2015b) A recyclable metal-organic framework MOF-199 catalyst in coupling and cyclization of β-bromo-α,β-unsaturated carboxylic acids with terminal alkynes leading to alkylidenefuranones. J Organomet Chem 791:13–17. https://doi.org/10.1016/j.jorganchem.2015.05.040
Horinouchi S, Beppu T (1994) A-factor as a microbial hormone that controls cellular differentiation and secondary metabolism in Streptomyces griseus. Mol Microbiol 12:859–864. https://doi.org/10.1111/j.1365-2958.1994.tb01073.x
Hou F, Wang XC, Quan ZJ (2018) Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols. Org Biomol Chem 16:9472–9476. https://doi.org/10.1039/C8OB02539H
Iinuma Y, Kahnt A, Mutzel A, Böge O, Herrmann H (2013) Ozone-driven secondary organic aerosol production chain. Environ Sci Technol 47:3639–3647. https://doi.org/10.1021/es305156z
Kristensen K, Enggrob KL, King SM, Worton DR, Platt SM, Mortensen R, Rosenoern T, Surratt JD, Bilde M, Goldstein AH, Glasius M (2013) Formation and occurrence of dimer esters of pinene oxidation products in atmospheric aerosols. Atmos Chem Phys 13:3763–3776. https://doi.org/10.5194/acp-13-3763-2013
Lawrence WT (1899) LI.—Synthesis and preparation of terebic and terpenylic acids. J Chem Soc Trans 75:527–533. https://doi.org/10.1039/CT8997500527
Rajagopalan A, Lara M, Kroutil W (2013) Oxidative alkene cleavage by chemical and enzymatic methods. Adv Synth Catal 355:3321–3335. https://doi.org/10.1002/adsc.201300882
Sato K, Jia T, Tanabe K, Morino Y, Kajii Y, Imamura T (2016) Terpenylic acid and nine-carbon multifunctional compounds formed during the aging of β-pinene ozonolysis secondary organic aerosol. Atmos Environ 130:127–135. https://doi.org/10.1016/j.atmosenv.2015.08.047
Silverman GS, Rakita PE (1996) Handbook of Grignard reagents. CRC Press, Boca Raton
Spannring P, Bruijnincx PCA, Weckhuysen BM, Klein Gebbink RJM (2013) A metal-free, one-pot method for the oxidative cleavage of internal aliphatic alkenes into carboxylic acids. RSC Adv 3:6606–6613. https://doi.org/10.1039/C3RA40324F
Takano E (2006) γ-Butyrolactones: Streptomyces signalling molecules regulating antibiotic production and differentiation. Curr Opin Microbiol 9:287–294. https://doi.org/10.1016/j.mib.2006.04.003
Takeda A, Tsuboi S, Oota Y (1973) Chemistry of α-haloaldehydes. III. Reaction of 2-halo-2-methylpropanal with malonic esters in the presence of potassium carbonate. (Synthesis of γ-butyrolactones). J Org Chem 38:4148–4152. https://doi.org/10.1021/jo00963a010
Tokmadzhyan GG (2011) Synthesis of new pyrazole and triazole derivatives containing a saturated γ-lactone ring. Russ J Organ Chem 47:954–957. https://doi.org/10.1134/S1070428011060236
Witkowski B, Gierczak T (2014) Early stage composition of SOA produced by α-pinene/ozone reaction: α-Acyloxyhydroperoxy aldehydes and acidic dimers. Atmos Environ 95:59–70. https://doi.org/10.1016/j.atmosenv.2014.06.018
Yasmeen F, Vermeylen R, Szmigielski R, Iinuma Y, Böge O, Herrmann H, Maenhaut W, Claeys M (2010) Terpenylic acid and related compounds: Precursors for dimers in secondary organic aerosol from the ozonolysis of α- and β-pinene. Atmos Chem Phys 10:9383–9392. https://doi.org/10.5194/acp-10-9383-2
Acknowledgements
This research was supported by the FRIEND (Fine Particle Research Initiative in East Asia Considering National Differences) Project through the National Research Foundation of Korea (NRF) funded by the Ministry of Science and ICT (NRF-2020M3G1A1114560).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
All authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Dao, P.D.Q., Park, JH., Lim, HJ. et al. Synthesis of terpenylic acid and its analogues by oxidative cleavage and lactonization of cyclopentenyl carbinols. Chem. Pap. 76, 1885–1889 (2022). https://doi.org/10.1007/s11696-021-01964-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-021-01964-6