Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(18): 2865-2892
DOI: 10.1055/s-0030-1260168
DOI: 10.1055/s-0030-1260168
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of Polypropionate-Derived γ-Pyrone Natural Products
Further Information
Received
4 May 2011
Publication Date:
10 August 2011 (online)
Publication History
Publication Date:
10 August 2011 (online)
Abstract
Over the years a wide variety of γ-pyrone-containing natural products have been isolated and a number of their total syntheses accomplished. This review discusses a selection of synthetic strategies towards the total synthesis of some of these complex metabolites.
1 Introduction
2 Polyketide Biosynthesis
3 Common Methodology for γ-Pyrone Construction
4 Synthetic Approaches
5 Polyunsaturated γ-Pyrones
5.1 Conjugated Polyenes: Cyercenes and Placidenes
5.2 Non-Conjugated Polyenes: Actinopyrone and Verticipyrone
6 Polyoxygenated Side-Chain
6.1 Baconipyrones A-D, Siphonarins A and B
6.2 Auripyrones A and B
7 Nitrophenyl γ-Pyrones and Derivatives
7.1 Aureothin, N-Acetylaureothamine
8 Electrocyclisation Reactions in γ-Pyrone Natural Product Synthesis
8.1 The Tridachione Family
8.2 The Tridachiahydropyrones
8.3 Spectinabilin and the ‘SNF’ Compounds
9 Conclusions
Key words
γ-pyrones - polyketides - biomimetic synthesis - natural products - electrocyclisation reactions
- 1
Davies-Coleman MT.Garson MJ. Nat. Prod. Rep. 1998, 15: 477 -
2a
Beaudry CM.Malerich JP.Trauner D. Chem. Rev. 2005, 105: 4757 -
2b
García-Pajón CM.Collado IG. Nat. Prod. Rep. 2003, 20: 426 -
2c
Pawlik JR. Chem. Rev. 1993, 93: 1911 -
2d
O’Hagan D. Nat. Prod. Rep. 1992, 9: 447 -
2e
Bu’Lock JD. In Comprehensive Organic Chemistry Pergamon; Oxford: 1979. Vol. 5. p.927 -
3a
Sunazuka T.Οmura S. Chem. Rev. 2005, 105: 4559 -
3b
McGlacken GP.Fairlamb IJS. Nat. Prod. Rep. 2005, 22: 369 -
4a
Ireland C.Faulkner DJ. Tetrahedron 1981, 37 (Suppl. 1): 233 -
4b
Ireland C.Scheuer PJ. Science 1979, 205: 922 -
4c
Ireland C.Faulkner DJ.Finer JS.Clardy J. J. Am. Chem. Soc. 1979, 101: 1275 -
4d
Ireland C.Faulkner DJ.Solheim BA.Clardy J. J. Am. Chem. Soc. 1978, 100: 1002 -
5a
Faulkner DJ. In Ecological Roles of Marine Natural ProductsPaul VJ. Comstock Publishing Associates; Ithaca (NY, USA): 1992. p.119 -
5b
Faulkner DJ.Ghiselin MT. Mar. Ecol.: Prog. Ser. 1983, 13: 295 - 6
Vardaro RR.Di Marzo V.Crispino A.Cimino G. Tetrahedron 1991, 47: 5569 - 7
Wilk W.Waldmann H.Kaiser M. Bioorg. Med. Chem. 2009, 17: 2304 -
8a
Takahashi K.Tsuda E.Kurosawa K. J. Antibiot. 2001, 54: 548 -
8b
Kurosawa K.Takahashi K.Tsuda E. J. Antibiot. 2001, 54: 541 -
9a
Zuidema DR.Jones PB. J. Photochem. Photobiol., B 2006, 83: 137 -
9b
Zuidema DR.Jones PB. J. Nat. Prod. 2005, 68: 481 - 10
Weissman KJ. Methods Enzymol. 2009, 459: 3 -
11a
Werneburg M.Busch B.He J.Richter MEA.Xiang L.Moore BS.Roth M.Dahse H.-M.Hertweck C. J. Am. Chem. Soc. 2010, 132: 10407 -
11b
Busch B.Hertweck C. Phytochemistry 2009, 70: 1833 -
11c
Hertweck C. Angew. Chem., Int. Ed. 2009, 48: 4688 -
11d
Werneburg M.Hertweck C. ChemBioChem 2008, 9: 2064 -
11e
Müller M.He J.Hertweck C. ChemBioChem 2006, 7: 37 -
12a
Wang C.-Y.Wang B.-G.Bravers G.Guan H.-S.Proksch P.Ebel R. J. Nat. Prod. 2002, 65: 772 -
12b
Asolkar RN.Kamat VP.Kirtany JK. J. Chem. Res., Synop. 2001, 549 -
13a
Harris TM.Murphy GP.Poje A. J. Am. Chem. Soc. 1976, 98: 7733 -
13b
Dorman LC. J. Org. Chem. 1967, 32: 4105 -
13c
Light RJ.Hauser CR. J. Org. Chem. 1960, 25: 538 - 14
Yamamura S.Nishiyama S. Bull. Chem. Soc. Jpn. 1997, 70: 2025 -
15a
Arimoto H.Yokoyama R.Nakamura K.Okumura Y.Uemura D. Tetrahedron 1996, 52: 13901 -
15b
Arimoto H.Okumura Y.Nishiyama S.Yamamura S. Tetrahedron Lett. 1995, 36: 5357 -
16a
Rodriguez R.Adlington RM.Eade SJ.Walter MW.Baldwin JE.Moses JE. Tetrahedron 2007, 63: 4500 -
16b
Shimamura H.Sunazuka T.Izuhara T.Hirose T.Shiomi K.Οmura S. Org. Lett. 2007, 9: 65 -
16c
Jacobsen MF.Moses JE.Adlington RM.Baldwin JE. Org. Lett. 2005, 7: 641 -
16d
Moses J. E.Baldwin J. E.Adlington R. M. Tetrahedron 2004, 45: 6447 -
16e
Garey D.Ramirez M.-l.Gonzales S.Wertsching A.Tith S.Keefe K.Peña MR. J. Org. Chem. 1996, 61: 4853 -
16f
Ishibashi Y.Ohba S.Nishiyama S.Yamamura S. Tetrahedron Lett. 1996, 37: 2997 - 17
Beak P.Lee J.-K. J. Org. Chem. 1975, 40: 147 - 18
Hite M.Rinehart W.Braun W.Peck H. AIHA J. 1979, 40: 600 - 19
Koreeda M.Akagi H. Tetrahedron Lett. 1980, 21: 1197 - 20
Clawson RW.Söderberg BCG. Tetrahedron Lett. 2007, 48: 6019 - 21
Vardaro RR.Di Marzo V.Cimino G. Tetrahedron Lett. 1992, 33: 2875 - 22
Liang G.Miller AK.Trauner D. Org. Lett. 2005, 7: 819 - 23
Ui H.Shiomi K.Suzuki H.Hatano H.Morimoto H.Yamaguchi Y.Masuma R.Sunazuka T.Shimamura H.Sakamoto K.Kita K.Miyoshi H.Tomoda H.Οmura S. J. Antibiot. 2006, 59: 785 -
24a
Yano K.Yokoi K.Sato J.Oono J.Kouda T.Ogawa Y.Nakashima T. J. Antibiot. 1986, 39: 38 -
24b
Yano K.Yokoi K.Sato J.Oono J.Kouda T.Ogawa Y.Nakashima T. J. Antibiot. 1986, 39: 32 - 25
Taniguchi M.Wantanabe M.Nagai K.Suzumura K.-i.Suzuki K.-i.Tanaka A. J. Antibiot. 2000, 53: 844 - 26
Lipshutz BH.Amorelli B. Tetrahedron Lett. 2009, 50: 2144 -
27a
Hosokawa S.Yokota K.Imamura K.Suzuki Y.Kawarasaki M.Tatsuta K. Chem. Asian J. 2008, 3: 1415 -
27b
Hosokawa S.Yokota K.Imamura K.Suzuki Y.Kawarasaki M.Tatsuta K. Tetrahedron Lett. 2006, 47: 5415 - 28
Manker DC.Faulkner DJ.Stout TJ.Clardy J. J. Org. Chem. 1989, 54: 5371 -
29a
Garson MJ.Jones DD.Small CJ.Liang J.Clardy J. Tetrahedron Lett. 1994, 35: 6921 -
29b
Hochlowski JE.Coll JC.Faulkner DJ.Biskupiak JE.Ireland CM.Zheng Q.He C.Clardy J. J. Am. Chem. Soc. 1984, 106: 6748 - 30
Blanchfield JT.Brecknell DJ.Brereton IM.Garson MJ.Jones DD. Aust. J. Chem. 1994, 47: 2255 -
31a
Paterson I.Chen DY.-K.Aceña JL.Franklin AS. Org. Lett. 2000, 2: 1513 -
31b
Paterson I. Pure Appl. Chem. 1992, 64: 1821 -
32a
Gillingham DG.Hoveyda AH. Angew. Chem. Int. Ed. 2007, 46: 3860 -
32b
Cortez GA.Baxter CA.Schrock RR.Hoveyda AH. Org. Lett. 2007, 9: 2871 - 33
Yadav JS.Sathaiah K.Srinivas R. Tetrahedron 2009, 65: 3545 - 34
Beye GE.Ward DE. J. Am. Chem. Soc. 2010, 132: 7210 - 35
Beye GE.Goodman JM.Ward DE. Org. Lett. 2009, 11: 1373 -
36a
Passacantilli P.Centore C.Ciliberti E.Leonelli F.Piancatelli G. Eur. J. Org. Chem. 2006, 3097 -
36b
Bettelli E.Cherubini P.D’Andrea P.Passacantilli P.Piancatelli G. Tetrahedron 1998, 54: 6011 - 37
Ward DE.Sales M.Man CC.Shen J.Sasmal PK.Guo C. J. Org. Chem. 2002, 67: 1618 - 38
Ward DE.Jheengut V.Beye GE. J. Org. Chem. 2006, 71: 8989 - 39
Paterson I.Chen DY.-K.Franklin AS. Org. Lett. 2002, 4: 391 - 40
Suenaga K.Kigoshi H.Yamada K. Tetrahedron Lett. 1996, 37: 5151 - 41
Lister T.Perkins MV. Angew. Chem. Int. Ed. 2006, 45: 2560 -
42a
Perkins MV.Sampson RA.Joannou J.Taylor MR. Tetrahedron Lett. 2006, 47: 3791 -
42b
Perkins MV.Jahangiri S.Taylor MR. Tetrahedron Lett. 2006, 47: 2025 - 43
Jung ME.Salehi-Rad R. Angew. Chem. Int. Ed. 2009, 48: 8766 - 44
Hayakawa I.Takemura T.Fukasawa E.Ebihara Y.Sato N.Nakamura T.Suenaga K.Kigoshi H. Angew. Chem. Int. Ed. 2010, 49: 2401 - 45
Jung ME.Chaumontet M.Salehi-Rad R. Org. Lett. 2010, 12: 2872 -
46a
He J.Hertweck C. Chem. Biol. 2003, 10: 1225 -
46b
He J.Müller M.Hertweck C. J. Am. Chem. Soc. 2004, 126: 16742 -
46c
He J.Hertweck C. J. Am. Chem. Soc. 2004, 126: 3694 -
47a
Schwartz JL.Tishler M.Arison BH.Shafer HM.Οmura S. J. Antibiot. 1976, 29: 236 -
47b
Oishi H.Hosogawa T.Okutomi T.Suzuki K.Ando K. Agric. Biol. Chem. 1969, 33: 1790 -
47c
Hirata Y.Nakata H.Yamada K.Okuhara K.Naito T. Tetrahedron 1961, 14: 252 -
47d
Maeda K. J. Antibiot. 1953, 6: 137 - 48
Liang G.Seiple IB.Trauner D. Org. Lett. 2005, 7: 2837 -
49a
Eade SJ.Walter MW.Byrne C.Odell B.Rodriguez R.Baldwin JE.Adlington RM.Moses JE. J. Org. Chem. 2008, 73: 4830 -
49b
Moses JE.Adlington RM.Rodriguez R.Eade SJ.Baldwin JE. Chem. Commun. 2005, 1687 -
50a
Jacobsen MF.Moses JE.Adlington RM.Baldwin JE. Tetrahedron 2006, 62: 1675 -
50b
Jacobsen MF.Moses JE.Adlington RM.Baldwin JE. Org. Lett. 2005, 7: 2473 -
50c
Moses JE.Baldwin JE.Marquez R.Adlington RM.Cowley AR. Org. Lett. 2002, 4: 3731 -
51a
Moses JE.Baldwin JE.Marquez R.Adlington RM.Claridge TDW.Odell B. Org. Lett. 2003, 5: 661 -
51b
Moses JE.Baldwin JE.Adlington RM.Cowley AR.Marquez R. Tetrahedron Lett. 2003, 44: 6625 -
51c
Brückner S.Baldwin JE.Moses JE.Adlington RM.Cowley AR. Tetrahedron Lett. 2003, 44: 7471 -
51d
Moses JE.Baldwin JE.Brückner S.Eade SJ.Adlington RM. Org. Biomol. Chem. 2003, 1: 3670 -
52a
Sharma P.Moses JE. Synlett 2010, 525 -
52b
Sharma P.Lygo B.Lewis W.Moses JE. J. Am. Chem. Soc. 2009, 131: 5966 -
52c
Sharma P.Griffiths N.Moses JE. Org. Lett. 2008, 10: 4025 -
53ax
Miller AK.Trauner D. Angew. Chem. Int. Ed. 2005, 44: 4602 -
53b
Beaudry CM.Trauner D. Org. Lett. 2005, 7: 4475 -
53c
Barbarow JE.Miller AK.Trauner D. Org. Lett. 2005, 7: 2901 -
53d
Miller AK.Byun DH.Beaudry CM.Trauner D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 12019 -
53e
Barbarow JE.Beaudry CM.Trauner D. Org. Lett. 2002, 4: 2221 - 54
Nicolaou KC.Petasis NA.Zipkin RE.Uenishi J. J. Am. Chem. Soc. 1982, 104: 5555 ; and references therein -
55a
Fu X.Hong EP.Schmitz FJ. Tetrahedron 2000, 56: 8989 -
55b
Gavagnin M.Spinella A.Castelluccio F.Cimino G.Marin A. J. Nat. Prod. 1994, 57: 298 -
55c
Ksebati MB.Schmitz FJ. J. Org. Chem. 1985, 50: 5637 - 56
Miller AK.Trauner D. Synlett 2006, 2295 - 57
Burnley J.Ralph M.Sharma P.Moses JE. In Biomimetic Organic SynthesisPoupon E.Nay B. Wiley-VCH; Weinheim: 2011. Chap. 16. doi: 10.1002/9783527634606.ch16 - 58
Gavagnin M.Mollo E.Cimino G.Ortea J. Tetrahedron Lett. 1996, 37: 4259 -
59a
Jeffery DW.Perkins MV.White JM. Org. Lett. 2005, 7: 1581 -
59b
Jeffery DW.Perkins MV.White JM. Org. Lett. 2005, 7: 407 - 60
Kakinuma K.Hanson CA.Rinehart KL. Tetrahedron 1976, 32: 217 - 61
Banfield JE.Black DSt. C.Johns SR.Willing RI. Aust. J. Chem. 1982, 35: 2247 - 62
Parker KA.Lim Y.-H. J. Am. Chem. Soc. 2004, 126: 15968 - 63
Müller M.Kusebauch B.Liang G.Beaudry CM.Trauner D.Hertweck C. Angew. Chem. Int. Ed. 2006, 45: 7835