A concise and straightforward approach to total synthesis of (+)-Strictifolione and formal synthesis of Cryptofolione via a unified strategy

References

• (a) Jodynis-Liebert, J.; Murias, M.; Błoszyk, E. Effect of Sesquiterpene Lactones on Antioxidant Enzymes and Some Drug-metabolizing Enzymes in Rat Liver and Kidney. Planta Med. 2000, 66, 199-205. DOI: 10.1055/s-2000-8566. (b) Drewes, S. E.; Horn, M. H.; Mavi, S. Cryptocarya Liebertiana and Ocotea Bullata—Their Phytochemical Relationship. S. Phytochemistry. 1997, 44, 437. DOI: 10.1016/S0031-9422(96)00464-5 . (c) Zschocke, S.; van Staden, J. J. Cryptocarya Species-Substitute Plants for Ocotea Bullata? A Pharmacological Investigation in Terms of Cyclooxygenase-1 and -2 Inhibition. J. Ethnopharmacol. 2000, 71, 473. DOI: 10.1016/S0378-8741(00)00183-5. (d) Hawariah, A.; Stanslas, J. In Vitro Response of Human Breast Cancer Cell Lines to the Growth-inhibitory Effects of Styrylpyrone Derivative (SPD) and Assessment of its Antiestrogenicity. Anticancer Res. 1998, 18, 4383. (e) Pihie, A. H. L.; Stanslas, J.; Din, L. B. Non-Steroid Receptor-mediated Antiproliferative Activity of Styrylpyrone Derivative in Human Breast Cancer Cell lines. Anticancer Res. 1998, 18, 1739. (f) Ee, Y. S.; Lai, L. C.; Reimann, K.; Lim, P. K. Effect of Transforming Growth Factor-beta1 on Oestrogen Metabolism in MCF-7 and MDA-MB-231 Breast Cancer Cell lines. Oncol. Rep. 1999, 6, 843. DOI: 10.3892/or.6.4.843.
   PubMed Web of Science ®Google Scholar
• Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K. Absolute Configuration of Two New 6-Alkylatedα-Pyrones (=2H-Pyran-2-ones) fromRavensara Crassifolia. HCA. 2001, 84, 3470-3476. DOI: 10.1002/1522-2675(20011114)84:11<3470::AID-HLCA3470>3.0.CO;2-K.
   Google Scholar
• Fu, T. X.; Sévenet, T.; Hamid, A.; Hadi, A.; Remy, F.; Pais, M. Kurzilactone from Cryptocarya kurzii.Phytochemistry. 1993, 33, 1272. DOI: 10.1016/0031-9422(93)85065-Y.
   Web of Science ®Google Scholar
• Echeverri, F.; Arango, V.; Quiñones, W.; Torres, F.; Escobar, G.; Rosero, Y.; Archbold, R. Passifloricins, polyketides alpha-pyrones from Passiflora Foetida resin. Phytochemistry. 2001, 56, 881-885. DOI: 10.1016/S0031-9422(00)00478-7.
   PubMed Web of Science ®Google Scholar
• Bohlmann, F.; Suwita, A. Ein Neues Bisabolen-Derivat Und Ein Neues Dihydro Kaffeesäure-Derivat Aus Tarchonanthus Trilobus. Phytochemistry. 1979, 18, 677-679. DOI: 10.1016/S0031-9422(00)84293-4.
   Web of Science ®Google Scholar
• Juliawaty, L. D.; Kitajima, M.; Takayama, H.; Achmad, S. A.; Aimi, N. A 6-substituted-5,6-dihydro-2-pyrone from Cryptocarya Strictifolia. Phytochemistry. 2000, 54, 989-993. DOI: 10.1016/S0031-9422(00)00077-7.
   PubMed Web of Science ®Google Scholar
• (a) Juliawaty, L. D.; Watanabe, Y.; Kitajima, M.; Achmad, S. A.; Takayama, H.; Aimi, N. First Total Synthesis and Determination of the Absolute Configuration of Strictifolione, a New 6-(ω-Phenylalkenyl)-5,6-dihydro-α-pyrone, isolated from Cryptocarya Strictifolia. Tetrahedron Lett. 2002, 43, 8657-8660. DOI: 10.1016/S0040-4039(02)02181-0.
   Web of Science ®Google Scholar
  (b) Bouz, B. S.; Cossy, J. Total Synthesis of (+)-Strictifolione. Org. Lett. 2003, 5, 1995-1997. DOI: 10.1021/ol034619s.
   PubMedGoogle Scholar
  (c) Tosaki, S.-Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Catalytic Asymmetric Synthesis of Both Syn- and Anti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/Alpha-Pyrone Natural Product Synthesis. Org. Lett. 2003, 5, 495-498. DOI: 10.1021/ol0273708.
   PubMed Web of Science ®Google Scholar
  (d) Enders, D.; Lenzen, A.; Muller, M. Efficient Asymmetric Syntheses of (+)-Strictifolione. Synthesis. 2004, 2004, 1486-1496. DOI: 10.1055/s-2004-822387.
   Google Scholar
  (e) Ramana, C. V.; Raghupathi, N.; Gurjar, M. K.; Chorghade, M. S. A Carbohydrate-based Approach for the Total Synthesis of Strictifolione. Tetrahedron Lett. 2005, 46, 4073-4075. DOI: 10.1016/j.tetlet.2005.04.031.
   Web of Science ®Google Scholar
  (f) Sabitha, G.; Fatima, N.; Gopal, P.; Reddy, C. N.; Yadav, J. S. Stereoselective Total Synthesis of (+)-Strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one by Prins Reaction and Olefin Cross-Metathesis. Tetrahedron Asymmetry. 2009, 20, 184-191. DOI: 10.1016/j.tetasy.2008.12.004.
   Google Scholar
  (g) Kumar, P.; Pandey, M.; Gupta, P.; Naidu, S. V.; Dhavale, D. D. Enantio- and Diastereocontrolled Total Synthesis of (+)-Strictifolione. Eur. J. Org. Chem. 2010, 2010, 6993-7004. DOI: 10.1002/ejoc.201001221.
   Google Scholar
  (h) Das, B.; Veeranjaneyulu, B.; Balasubramanyam, P.; Srilatha, M. Stereoselective Total Synthesis of (+)-Strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydro-10-phenyl-1-decenyl)-5,6-dihydro-2H-2-Pyrone. Tetrahedron: Asymmetry 2010, 21, 2762-2767.
   Google Scholar
  (i) Tang, S.; Xie, X.; Wang, X.; He, L.; Xu, K.; She, X. Concise Total Syntheses of (+)-Strictifolione and (6R)-6-[(4R,6R)-4,6-Dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2 H -pyran-2-One. J. Org. Chem. 2010, 75, 8234-8240. DOI: 10.1021/jo101875w.
   PubMed Web of Science ®Google Scholar
  (j) Ghadigaonkar, S.; Koli, M. R.; Gamre, S. S.; Choudhary, K. M.; Chattopadhyay, S.; Sharma, A. A Chemoenzymatic Asymmetric Synthesis of (+)-Strictifolione. Tetrahedron Asymmetry. 2012, 23, 1093-1099. DOI: 10.1016/j.tetasy.2012.06.015.
   Google Scholar
  (k) Jayasinghe, S.; Venukadasula, P. K. M.; Hanson, P. R. An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product. Org. Lett. 2014, 16, 122-125. DOI: 10.1021/ol403110p.
   PubMed Web of Science ®Google Scholar
  (l) Wang, X. J.; Wang, G. P.; Huang, S. P.; Zhang, Z. M.; Liu, S.; Chen, S. P. Natural product (+)-Strictifolione synthetic method. CN105254604 A 2016,
   Google Scholar
• (a) Sehlapelo, B. M.; Drewes, S. E.; Scott-Shaw, R. A 6-substituted 5,6-dihydro-α-pyrone from Two Species of Cryptocarya. Phytochemistry. 1994, 37, 847. DOI: 10.1016/S0031-9422(00)90368-6. (b) Cavalheiro, A. J.; Yoshida, M. 6-[Omega-Arylalkenyl]-5,6-Dihydro-Alpha-Pyrones from Cryptocarya Moschata (Lauraceae). Phytochemistry. 2000, 53, 811. DOI:10.1016/S0031-9422(99)00532-4. (c) Nehme, C. J.; Bastos, W. L.; De Araújo, A. J.; Cavalheiro, A. J. An HPLC-PAD Method to Analyse Flavonoid Glycosides and Styrylpyrones from Cryptocarya Species (lauraceae). Phytochem. Anal. 2005, 16, 93. DOI: 10.1002/pca.818.
   Web of Science ®Google Scholar
• (a) Matsuoka, Y.; Aikawa, K.; Irie, R.; Katsuki, T. Asymmetric Synthesis of Cryptofolione and Determination of Its Absolute Configuration. Heterocycles. 2005, 66, 187-194. DOI: 10.3987/COM-05-S(K)73.
   Web of Science ®Google Scholar
  (b) Sabitha, G.; Reddy, S. S. S.; Reddy, D. V.; Bhaskar, V.; Yadav, J. S. Stereoselective Approaches to the Total Synthesis of (6R,4′S,6′R)-Cryptofolione. Synthesis. 2010, 2010, 3453-3460. DOI: 10.1055/s-0030-1258215.
   Google Scholar
  (c) Balasubramanyam, P.; Reddy, G. C.; Salvanna, N.; Das, B. Efficient Stereoselective Total Synthesis of (+)-Cryptofolione and the FirstSynthesis of (–)-Cryptocaryalactone. Synthesis. 2011, 3706-3710. DOI: 10.1055/s-0030-1260246.
   Web of Science ®Google Scholar
  (d) Das, B.; Nagendra, S.; Reddy, C. R. Stereoselective Total Synthesis of (+)-Cryptofolione and (+)-Goniothalamin. Tetrahedron Asymmetry. 2011, 22, 1249-1254. DOI: 10.1016/j.tetasy.2011.06.029.
   Google Scholar
  (e) Kumar, R. N.; Meshram, H. M. Total Synthesis of (−)-Diospongin a and (+)-Cryptofolione via Asymmetric Aldol Reaction. Tetrahedron Lett. 2011, 52, 1003-1007. DOI: 10.1016/j.tetlet.2010.12.070.
   Web of Science ®Google Scholar
  (f) Yadav, J. S.; Ganganna, B.; Bhunia, D. C. First Stereoselective Total Synthesis of Cryptomoscatone D2 and Syntheses of (5R,7S)-Kurzilactone and (+)-Cryptofolione by an Asymmetric Acetate Aldol Approach. Synthesis. 2012, 44, 1365-1372. DOI: 10.1055/s-0031-1290771.
   Web of Science ®Google Scholar
• Schmeda-Hirschmann, G.; Astudillo, L.; Bastida, J.; Codina, C.; Rojas de Arias, A.; Ferreira, M. E.; Inchaustti, A.; Yaluff, G. Cryptofolione Derivatives from Cryptocarya Alba fruits. J. Pharm. Pharmacol. 2001, 53, 563. DOI: 10.1211/0022357011775686.
   PubMed Web of Science ®Google Scholar
• Huang, S. P.; Liu, D. W.; Tang, L. J.; Huang, F. F.; Yang, W.; Wang, X. J. A Concise and Versatile Total Synthesis of All Stereoisomers of Tarchonanthuslactone. Synlett. 2015, 26, 2019-2023. DOI: 10.1055/s-0034-1378784.
   Web of Science ®Google Scholar
• (a) Li, C. J.; Chan, T. H. Organometallic Reactions in Aqueous Media with Indium. Tetrahedron Lett. 1991, 32, 7017-7020. DOI: 10.1016/0040-4039(91)85028-4.
   Web of Science ®Google Scholar
  (b) Li, C. J. Aqueous Barbier-Grignard Type Reaction: Scope, Mechanism, and Synthetic Applications. Tetrahedron. 1996, 52, 5643-5668. DOI: 10.1016/0040-4020(95)01056-4.
   Web of Science ®Google Scholar
• (a) Lin, S. J.; Zhang, J. T.; Zhang, Z. B.; Xu, T. X.; Huang, S. P.; Wang, X. J. Asymmetric Total Synthesis of Ieodomycin B. Mar. Drugs. 2017, 15, 17. DOI: 10.3390/md15010017. (b) Hodge, M. B.; Olivo, H. F. Stereoselective Aldol Additions of Titanium Enolates of N-acetyl-4-isopropyl-Thiazolidinethione. Tetrahedron. 2004, 60, 9397-9403. DOI: 10.1016/j.tet.2004.08.008.
   Web of Science ®Google Scholar
• For examples: (a) Soriente, A.; De Rosa, M.; Villano, R.; Scettri, A. Enantioselective Aldol Condensation of 1,3-bis-(Trimethylsilyloxy)-1-Methoxy-Buta-1,3-Diene Promoted by Chiral Ti(IV)/BINOL Complex. Tetrahedron Asymmetry. 2000, 11, 2255-2258. DOI: 10.1016/S0957-4166(00)00200-7.
   Web of Science ®Google Scholar
  (b) Soriente, A.; De Rosa, M.; Stanzione, M.; Villano, R.; Scettri, A. An Efficient Asymmetric Aldol Reaction of Chan's Diene Promoted by Chiral Ti(IV)-BINOL Complex. Tetrahedron Asymmetry. 2001, 12, 959-963. DOI: 10.1016/S0957-4166(01)00150-1.
   Google Scholar
• Wolberg, M.; Dassen, B. H. N.; Schürmann, M.; Jennewein, S.; Wubbolts, M. G.; Schoemaker, H. E.; Mink, D. Large-Scale Synthesis of New Pyranoid Building Blocks Based on Aldolase-Catalysed Carbon-Carbon Bond Formation. Adv. Synth. Catal. 2008, 350, 1751-1759. DOI: 10.1002/adsc.200800224.
   Web of Science ®Google Scholar