Stereoselective Synthesis of (-)-Tetrahydropyrenophorol

Vyasabhattar Ramanujan, Shaik Sadikha, Chebolu Naga Sesha Sai Pavan Kumar

Abstract


Tetrahydropyrenophorol, an interesting macrodiolide was isolated from the plant Fagonia cretica. The total synthesis of (-)-1-tetrahydropyrenophorol was achieved in an elegant and linear manner from readily accessible racemic epoxide. The archetypal reactions include regioselective opening of epoxide, Sharpless asymmetric dihydroxylation and Mitsunobu cyclodimerisation to construct the requisite 16-membered bis-lactone. Synthetic approach demonstrated here is very simple and can be used for the syntheses of related compounds in economic and highly stereoselective way.


Keywords


Macrodiolide; sharpless asymmetric dihydroxylation; Mitsunobu reaction; stereoselectivity

Full Text:

PDF (1,718 kB)

References


K. C. Nicolaou, S. A. Snyder, Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 11929 (https://doi.org/10.1073/pnas.0403799101)

Z. Kis, P. Furger, H. Sigg, Experientia 25 (1969) 123 (https://doi.org/10.1007/BF01899073)

W. Zhang, K. Krohn, H. Egold, S. Draeger, B. Schulz, Eur. J. Org. Chem. 2008 (2008) 4320 (https://doi.org/10.1002/ejoc.200800404)

S. Nozoe, K. Hira, K. Tsuda, K. Ishibashi, J. F. Grove, Tetrahedron Lett. 6 (1965) 4675 https://doi.org/10.1016/S0040-4039(01)84033-8

R. Kind, A. Zeeck, S. Grabley, R. Thiericke, M. Zerlin, J. Nat. Prod. 59 (1996) 539 https://doi.org/10.1021/np960083q

E. L. Ghisalberti, J. R. Hargreaves, B. W. Skelton, A. H. White, Aust. J. Chem. 55 (2002) 233 https://doi.org/10.1071/CH01197

C. Christner, G. Kullertz, G. Fischer, M. Zerlin, S. Grabley, R. Thiericke, A. Taddei, A. Zeeck, J. Antibiot. 51 (1998) 368 https://doi.org/10.7164/antibiotics.51.368

M. A. Kastanias, M. Chrysayi-Tokousbalides, Pest Manage. Sci. 56 (2000) 227 https://doi.org/10.1002/(SICI)1526-4998(200003)56:3<227::AID-PS115>3.0.CO;2-A

M. A. Kastanias, Chrysayi-Tokousbalides, J. Agric. Food Chem. 53 (2005) 5943 https://doi.org/10.1021/jf050792m

F. Sugawara, G. A. Strobel, Plant Sci. 43 (1986) 1 https://doi.org/10.1016/0168-9452(86)90099-3

K. Shimomura, M. G. Mullinix, T. Kakunaga, H. Fujiki, T. Sugimura, Science 222 (1983) 1242 DOI: 10.1126/science.6316505

K. Krohn, U. Farooq, U. Flörke, B. Schulz, S. Draeger, G. Pescitelli, P. Salvadori, S. Antus, T. Kurtán, Eur. J. Org. Chem. (2007) 3206 https://doi.org/10.1002/ejoc.200601128

H. –S. Oh, H. –Y. Kang, Bull. Korean Chem. Soc. 32 (2011) 2869 DOI: 10.5012/bkcs.2011.32.8.2869

B. Pratapareddy, R. Sreenivasulu, T. Pradeepkumar, I. Hatti, M. V. B. Rao, V. N. Kumar, R. R. Raju, Monatsh Chem. 148 (2017) 751 https://doi.org/10.1007/s00706-016-1754-2

M. Mahesh, B. Raman, K. V. Sastry, M. Sridhar, G. Sridhar, Arkivoc (iii) (2018) 112 https://doi.org/10.24820/ark.5550190.p010.316

B. M. Trost, A. Quintard, Angew. Chem. Int. Ed. 51 (2012) 6704 https://dx.doi.org/10.1002/anie.201203035

V. B. Ramanujan, R. Sreenivasulu, M. Chavali, Ch. N. S. S. P. Kumar, Monatsh Chem. 148 (2017) 1865 DOI: 10.1007/s00706-017-1947-3

V. B. Ramanujan, Ch. N. S. S. P. Kumar, Arkivoc (vii) (2018) 332 DOI: https://doi.org/10.24820/ark.5550190.p010.703

I. V. P. Raj, A. Sudalai, Tetrahedron Letters 49 (2008) 2646 https://doi.org/10.1016/j.tetlet.2008.02.064

H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 94 (1994) 2483 https://doi.org/10.1021/cr00032a009

K. B. Sharpless, W. Amberg, M. Beller, H. Chen, J. Hartung, Y. Kawanami, D. Lübben, E. Manoury, Y. Ogino, T. Shibata, T. Ukita. J. Org. Chem. 56 (1991) 4585 https://doi.org/10.1021/jo00015a001

M. M. Heravi, V. Zadsirjan, M. Esfandyari, T. B. Lashaki. Tetrahedron: Asymmetry 28 (2017) 987 https://doi.org/10.1016/j.tetasy.2017.07.004

L. Huang, N. Teumelsan, X. Huang, Chem. Eur. J. 12 (2006) 5246 https://doi.org/10.1002/chem.200600290

J. B. Epp, T. S. Widlanski J. Org. Chem. 64 (1999) 293 https://doi.org/10.1021/jo981316g

H. Gerlach, K. Oertle, A. Thalmann, Helv. Chim. Acta 60 (1977) 2860 https://doi.org/10.1002/hlca.19770600838




DOI: https://doi.org/10.2298/JSC190823040R

Copyright (c) 2020 Journal of the Serbian Chemical Society

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

IMPACT FACTOR 1.097
5 Year Impact Factor 1.023
(
138 of 177 journals)