References
- (a) Ito, S.; Matsuya, T.; Omura, S.; Otani, M.; Nakagawa, A.; Takeshima, H.; Iwai, Y.; Ohtani, M.; Hata, T.A New Antibiotic, Kinamycin. J. Antibiot.1970, 23, 315-317. DOI: 10.7164/antibiotics.23.315.; (b) Hata, T.; Omura, S.; Iwai, Y.; Nakagawa, A.; Otani, M.; Ito, S.; Matsuya, T.A New Antibiotic, Kinamycin: Fermentation, Isolation, Purification and Properties. J. Antibiot.1971, 24, 353-359. DOI: 10.7164/antibiotics.24.353.
- He, H.; Ding, W. D.; Bernan, V. S.; Richardson, A. D.; Ireland, C. M.; Greenstein, M.; Ellestad, G. A.; Carter, G. T.Lomaiviticins A and B, Potent Antitumor Antibiotics from Micromonosporalomaivitiensis. J. Am. Chem. Soc.2001, 123, 5362-5363. DOI: 10.1021/ja010129o.
- Lubken, T.; Schmidt, J.; Porzel, A.; Arnold, N.; Wessjohann, L.Hygrophorones A-G: fungicidal Cyclopentenones from Hygrophorus Species (Basidiomycetes). Phytochemistry2004, 65, 1061-1071. DOI: 10.1016/j.phytochem.2004.01.023.
- (a) Umino, K.; Furumai, T.; Matsuzawa, N.; Awataguchi, Y.; Ito, Y.; Okuda, T.Studies on Pentenomycins. I. J. Antibiot.1973, 26, 506-512. DOI: 10.7164/antibiotics.26.506.; (b) Umino, K.; Takeda, N.; Ito, Y.; Okuda, T.Studies on Pentenomycins. II. The Structures of Pentenomycin I and II, New Antibiotics. J. Antibiot. 1974, 22, 1233-1238. DOI: 10.1248/cpb.22.1233.
- Aitken, D. J.; Eijsberg, H.; Frongia, A.; Ollivier, J.; Piras, P. P.Recent Progress in the Synthetic Assembly of 2-Cyclopentenones. Synthesis2013, 46, 1-24. DOI: 10.1055/s-0033-1340414.
- Bette, E.; Otto, A.; Drager, T.; Merzweiler, K.; Arnold, N.; Wessjohann, L.; Westermann, B.Isolation and Asymmetric Total Synthesis of Fungal Secondary Metabolite Hygrophorone B 12. Eur. J. Org. Chem.2015, 2015, 2357-2365. DOI: 10.1002/ejoc.201403455.
- Otto, A.; Porzel, A.; Schmidt, J.; Brandt, W.; Wessjohann, L.; Arnold, N.Structure and Absolute Configuration of Pseudohygrophorones a 12 and B 12, Alkyl Cyclohexenone Derivatives from Hygrophorus Abieticola (Basidiomycetes). J. Nat. Prod.2016, 79, 74-80. DOI: 10.1021/acs.jnatprod.5b00675.
- Otto, A.; Porzel, A.; Westermann, B.; Brandt, W.; Wessjohann, L.; Arnold, N.Structural and Stereochemical Elucidation of New Hygrophorones from Hygrophorus Abieticola (Basidiomycetes). Tetrahedron2017, 73, 1682-1690. DOI: 10.1016/j.tet.2017.02.013.
- (a) Yamamoto, Y.; Mori, N.; Watanabe, H.; Takikawa, H.First Synthesis of (±)-Pseudohygrophorone A12, an Anti-Fungal Cyclohexenone Derivative Isolated from Hygrophorus Abieticola. Tet. Lett.2018, 59, 3503-3505. DOI: 10.1016/j.tetlet.2018.08.027.; (b) Yamamoto, Y.; Ogura, Y.; Watanabe, H.; Takikawa, H.First Synthesis of Both Enantiomers of Pseudohygrophorone A12, an anti-Fungal Cyclohexenone Derivative Isolated from Hygrophorus Abieticola. Tetrahydron2019, 75, 130528. DOI: 10.1016/j.tet.2019.130528.
- (a) Trost, B. M.; Romero, A. G.Synthesis of Optically Active Isoquinuclidines Utilizing a Diastereoselectivity Control Element. J. Org. Chem.1986, 51, 2332-2342. DOI: 10.1021/jo00362a030. (b) Barros, M. T.; Maycock, C. D.; Ventura, M. R.The Enantioselective Total Synthesis of Epoformin and Analogues. Tetrahedron1999, 55, 3233. DOI: 10.1016/S0040-4020(98)01136-3.
- Gholap, S. L.; Woo, C. M.; Ravikumar, P. C.; Herzon, S. B.Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A. Org. Lett.2009, 11, 4322-4325. DOI: 10.1021/ol901710b.
- The stereochemistry of newly formed chiral centre at C-6 in α-hydroxyketones 12 and 13 were assigned after deprotection of acetonide functionality and comparison of 1H and 13C NMR spectral data of (+)-1 with ent-1 and (+)-2 with ent-2 in CDCl3; See SI, table-1 and table-2.
- In this reaction, 4-5% of aromatized product 5b was isolated and confirmed by 1H NMR spectroscopy.