Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 23, 2009 - Issue 3
263
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Hemisynthesis of two marine cheilanthane sesterterpenes from (−)-sclareol: First enantioselective synthesis of petrosaspongiolide R

, , , &
Pages 256-263 | Received 17 Apr 2007, Accepted 18 Feb 2008, Published online: 29 Oct 2009

References

  • Basabe , P , Delgado , S , Marcos , IS , Diez , D , Diego , A De Roman , M . 2005 . Synthesis of three marine natural sesterterpenolides from methyl isoanticopalate. First enantioselective synthesis of luffolide . Journal of Organic Chemistry , 70 : 9480 – 9485 .
  • Buchanan , MS , Edser , A , King , G , Whitmore , J and Quinn , RJ . 2001 . Cheilanthane sesterterpenes, protein kinase inhibitors, from a marine sponge of the genus Ircinia . Journal of Natural Products , 64 : 300 – 303 .
  • Fekih , AW , Gafsi , K , Ferreiro-Mederos , L and Hanquet , G . 2006 . Hemisynthesis of new labdane derivatives from (−)-sclareol . Natural Product Research, Part A: Structure and Synthesis , 20 : 887 – 895 .
  • Furuichi , N , Hata , T , Soetjipto , H , Kato , M and Katsumura , S . 2001 . Common synthetic strategy for optically active cyclic terpenoids having a 1,1,5-trimethyl-trans-decalin nucleus: syntheses of (+)-acuminolide, (−)-spongianolide A, and (+)-scalarenedial . Tetrahedron , 57 : 8425 – 8442 .
  • Gray , CA , Davies-Coleman , MT and Rivett , DEA . 2003 . An improved synthesis of rhinocerotinoic acid . Tetrahedron , 59 : 165 – 173 .
  • Hanquet , G and Lusinchi , X . 1997 . Oxygen transfer reactions from an oxaziridinium tetrafluoroborate salt to olefins . Tetrahedron , 53 : 13727 – 13738 .
  • Hata , T , Tanaka , K and Katsumura , S . 1999 . First synthesis of (−)-spongianolide A and B and determination of its absolute structure . Tetrahedron Letters , 40 : 1731 – 1734 .
  • Ishihara , K , Ishibashi , H and Yamamoto , H . 2001 . Enantioselective biomimetic cyclisation of homo(polyprenyl)arenes. A new entry to (+)-Podpcara-8,11,13-triene diterpenoids and (−)tetracyclic polyprenoid of sedimentary origin . Journal of American Chemical Society , 63 : 1505 – 1506 .
  • Monti , MC , Casapullo , A , Riccio , R and Gomez-Paloma , L . 2004 . Further insights on the structural aspects of PLA2 inhibition by g-hydroxybutenolide-containing natural products: A comparative study on petrosaspongiolides M-R . Bioorganic & Medicinal Chemistry , 12 : 1467 – 1474 .
  • Nair , MS and Anilkumar , AT . 1996 . Versatile chiral intermediates for terpenoids synthesis using lipase catalysed acylation . Tetrahedron: Asymmetry , 7 : 511 – 514 .
  • Parikh , J , Doering , W and von , E . 1967 . Sulfur trioxyde in the oxidation of alcohols by dimethylsulfoxide . Journal of American Chemical Society , 89 : 5505 – 5507 .
  • Randazzo , A , Debitus , C , Minale , L , Garcia Pastor , P , Alcaraz , MJ Paya , M . 1998 . Petrosaspongiolides M-R: New potent and selective phospholipase A2 inhibitors from the New Caledonian marine sponge Petrosaspongia nigra . Journal of Natural Products , 61 : 571 – 575 .
  • Shimizu , T , Hiranuma , S , Hayashibe , S and Yoshioka , H . 1991 . Nucleophilic reaction with methyl cyanoformate: A novel a-cyanomethylation and hydrocyanation of α, β-unsaturated carbonyl compounds . Synlett , 11 : 833 – 835 .
  • Tanimoto , H and Oritani , T . 1996 . Practical synthesis of ambrox from farnesyl acetate involving lipase catalyzed resolution . Tetrahedron: Asymmetry , 7 : 1695 – 1704 .
  • Urones , JG , Marcos , IS , Basabe , P , Gomez , A and Estrella , A . 1994 . Highly regioselective elimination of a ring–attached acetoxy group: Methyl ent-isocopalate from sclareol . Natural Product Letters , 5 : 217 – 220 .
  • Zoretic , PA , Fang , H , Ribeiro , AA and Dubay , G . 1998 . Synthesis of acuminolideand 17-O-acetylacuminolide from (+)-sclareolide . Journal of Organic Chemistry , 63 : 1156 – 1161 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.