Synthesis of Polyfunctional Drimanes from Drim-7,9(11)-diene and Drim-8-en-7-one

REFERENCES

• Jansen , B. J. M. ; de Groot , A. The occurence and biological activity of drimane sesquiterpenoids . Nat. Prod. Rep. 1991 , 8 , 309 – 318 .
   PubMed Web of Science ®Google Scholar
• Jansen , B. J. M. ; de Groot , A. Occurence, biological activity, and synthesis of drimane sesquiterpenoids . Nat. Prod. Rep. 2004 , 21 , 449 – 477 .
   PubMed Web of Science ®Google Scholar
• Nakano , T. ; Mailo , M. A. A novel, short synthesis of confertifolin . Synth. Commun. 1981 , 11 , 463 – 473
   Web of Science ®Google Scholar
• Nakano , T. ; Aguero , M. E. A new, efficient synthesis of (+)-isodrimenin. J. Chem. Soc. Perkin Trans. 1 1982, 1163–1164
   Google Scholar
• Nakano , T. ; Mailo , M. A. Reaction of (1S,6S)-1,7,7-trimethyl-2,3-dimethylene-trans-bicyclo[4.4.0]decane with thallium(III)acetate: A new route to (−)-warburganal and (+)-euryfurane . J. Chem. Soc., Perkin Trans. 1 1987 , 2137 – 2140
   Google Scholar
• Nakano , T. ; Villamizar , J. E. ; Mailo , M. A. Highly efficient synthesis of optically active drimanic sesquiterpenes, (+)-fuegin, (+)-epifutronolide (7β-hydroxyisodrimenin), and (+)-ketoisodrimenin . Tetrahedron 1999 , 55 , 1561 – 1568 .
   Web of Science ®Google Scholar
• Vlad , P. F. ; Ciocarlan , A. G. ; Coltsa , M. N. ; Deleanu , C. ; Costan , O. ; Simonov , Yu. A. ; Kravtsov , V. Ch. ; Lipkowski , J. ; Lis , T. ; De Groot , A. Photodegradation of some 14,15-bisnorlabdene-13-ones, derived from larixol: Synthesis of drimanic dienes with functional groups at C-6 . Tetrahedron 2006 , 62 , 8489 – 8497 .
   Web of Science ®Google Scholar
• Lithgow , A. M. ; Marcos , I. S. ; Basabe , P. ; Sexmero , J. ; Diez , D. ; Gomez , A. ; Estrella , A. ; Urones , J. G. Labdanolic acid as synthetic precursor of active drimanes . Nat. Prod. Lett. 1995 , 6 , 291 – 294 .
   Web of Science ®Google Scholar
• Cortés , M. ; Armstrong , V. ; Reyes , M. E. ; Lopez , J. ; Madariaga , E. Formal synthesis of ambrox and 9-epiambrox . Synth. Commun. 1996 , 26 , 1995 – 2002 .
   Web of Science ®Google Scholar
• Barrero , A. F. ; Alvarez-Manzaneda , E. J. ; Chahboun , R. Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes . Tetrahedron 1998 , 54 , 5635 – 5650 .
   Web of Science ®Google Scholar
• Akita , H. ; Nozawa , M. ; Mitsuda , A. ; Ohsawa , H. A convenient synthesis of (+)-albicanol based on enzymatic function: Total syntheses of (+)-albicanyl acetate, (−)-albicanyl 3,4-dihydroxycinnamate, (−)-drimenol, (−)-drimenin, and (−)-ambrox . Tetrahedron: Asymmetry 2000 , 11 , 1375 – 1388 .
   Web of Science ®Google Scholar
• Vlad , P. F. ; Aryku , A. N. ; Chokyrlan , A. G. Synthesis of (+)-drim-9(11)-en-8α -ol from sclareol . Russ. Chem. Bull. 2004 , 53 , 443 – 446 .
   Web of Science ®Google Scholar
• Alvarez-Manzaneda , E. J. ; Chahboun , R. ; Torres , E. C. ; Alvarez , E. ; Alvarez-Manzaneda , R. ; Haidour , A. ; Ramos , J. Triphenylphosphine-iodine: An efficient reagent for the regioselective dehydration of tertiary alcohols . Tetrahedron Lett. 2004 , 45 , 4453 – 4455 .
   Web of Science ®Google Scholar
• Vlad , P. F. ; Ciocarlan , A. G. ; Coltsa , M. N. ; Baranovsky , A. V. ; Kripach , N. B. Synthesis of drim-7,9(11)-diene and its hydroxylated derivatives . Synth. Commun. 2008 , 38 , 3960 – 3972 .
   Web of Science ®Google Scholar
• Aasen , A. J. ; Vogt , C. H. G. ; Enzel , C. R. Tobacco chemistry, 28: Structure and synthesis of drim-8-en-7-one, a new tobacco constituent . Acta Chem. Scand. 1975 , B29 , 51 – 55 .
   Google Scholar
• Vlad , P. F. ; Vorob'eva , E. A. Synthesis of drim-8-en-7-one . Chem. Nat. Compd. 1983 , 19 , 139 – 141 .
   Google Scholar
• Koltsa , M. N. ; Mironov , G. N. ; Malinovskii , S. T. ; Vlad , P. F. Synthesis of drim-8(9)-en-7-one, drim-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives from norambreinolide . Russ. Chem. Bull. 1996 , 45 , 208 – 214 .
   Web of Science ®Google Scholar
• Clennan , E. L. ; Pace , A. Advances in singlet oxygen chemistry . Tetrahedron 2005 , 61 , 6665 – 6691 .
   Web of Science ®Google Scholar
• Balci , M. Bicyclic endoperoxides and synthetic applications . Chem. Rev. 1981 , 81 , 91 – 108 .
   Web of Science ®Google Scholar
• Kulcitki , V. ; Ungur , N. ; Vlad , P. F. Superacidic low temperature cyclization of terpenyphenysulfones . Tetrahedron 1998 , 54 , 11925 .
   Web of Science ®Google Scholar
• Urones , J. G. ; Diez , D. ; Gomez , P. M. ; Marcos , I. S. ; Basabe , P. ; Moro , R. F. Chemistry of zamoranic acid, Part 10: Homochiral hemisynthesis of pereniporin A . J. Chem. Soc., Perkin Trans. 1 1997 , 11 , 1815 – 1818 .
   Google Scholar
• Urones , J. G. ; Marcos , I. S. ; Perez , B. G. ; Lithgow , A. M. ; Diez , D. ; Gomez , P. M. ; Basabe , P. ; Garrido , N. M. Chemistry of zamoranic acid, part IX: Homochiral synthesis of polygodial and warburganal from 17-acetoxy-7-labden-15-ol . Tetrahedron 1995 , 51 , 1845 – 1860 .
   Web of Science ®Google Scholar
• Boulin , B. ; Arreguy-San Miguel , B. ; Delmond , B. Le γ-pyronene: Synthone d'acces au safranal et precurseur d'intermediaires de synthese de la forskoline et du strigol. Tetrahedron 1998, 54, 2753–2762.
   Web of Science ®Google Scholar
• Vlad , P. F. ; Ciocarlan , A. G. ; Mironov , G. N. ; Coltsa , M. N. ; Simonov , Yu. A. ; Kravtsov , V. Ch. ; Lipkowski , J. Synthesis of 7α - and 7β-bromonorambreinolides from norambreinolide . Chem. J. Moldova 2007 , 2 , 114 – 118 .
   Google Scholar
• Timmermann , B. N. ; Hoffmann , J. J. ; Joland , S. D. ; Schram , K. H. Y. ; Klenck , R. E. ; Bates , R. B. Constituents of Chrysothamnus paniculatus (Compositae), 2: Chrysolic acid, a new labdane-derived diterpene with an aromatic B ring . J. Org. Chem. 1982 , 47 , 4114 – 4116 .
   Web of Science ®Google Scholar
• Urones , J. G. ; Marcos , I. S. ; Garrido , N. M. ; Moro , R. F. Fregenedadiol: A rearranged labdane from Halium viscosum . Phytochemistry 1990 , 29 , 3042 – 3044 .
   Web of Science ®Google Scholar
• Zdero , C. ; Bohlmann , F. ; Niemeyer , H. M. Seco-, nor-, normal, and rearranged labdanes from Haplopappus parvifolius . Phytochemistry 1991 , 30 , 3683 – 3691 .
   Web of Science ®Google Scholar
• Marcos , I. S. ; Jorge , A. ; Diez , D. ; Basabe , P. ; Lithgow , A. M. ; Sexmero , M. J. ; Garrido , N. M. ; Urones , J. G. Isofregenedadiol: A novel diterpenic diol from Halium viscosum . Phytochemistry 1996 , 41 , 1155 – 1157 .
   Web of Science ®Google Scholar
• Urones , J. G. ; Marcos , I. S. ; Basabe , P. ; Garrido , N. M. ; Jorge , A. ; Moro , R. F. ; Lithgow , A. M. Synthesis of fregenedadiol dimethyl ether . Nat. Prod. Lett. 1993 , 3 , 173 – 176 .
   Google Scholar
• Urones , J. G. ; Marcos , I. S. ; Basabe , P. ; Garrido , N. M. ; Jorge , A. ; Moro , R. F. ; Lithgow , A. M. Chemistry of 7-labden-3β,15-diol (I): Homochiral synthesis of fregenedadiol . Tetrahedron 1993 , 49 , 6079 – 6088 .
   Web of Science ®Google Scholar
• Urones , J. G. ; Jorge , A. ; Marcos , I. S. ; Basabe , P. ; Diez , D. ; Garrido , N. M. ; Lithgow , A. M. I2 rearrangement reaction: Synthesis of isofregenedane type diterpenoids . Tetrahedron. Lett. 1996 , 37 , 1659 – 1662 .
   Web of Science ®Google Scholar
• Marcos , I. S. ; Laderas , M. ; Diez , D. ; Basabe , P. ; Moro , R. F. ; Garrido , N. M. ; Urones , J. G. Synthesis and absolute configuration of (−)-chrysolic acid and (+)-isofregenedol . Tetrahedron. Lett. 2003 , 44 , 5419 – 5422 .
   Web of Science ®Google Scholar
• Marcos , I. S. ; Basabe , P. ; Laderas , M. ; Diez , D. ; Jorge , A. ; Rodilla , J. M. ; Moro , R. F. ; Lithgow , A. M. ; Barrata , I. G. ; Urones , J. G. Side-chain migration reaction and B aromatization in labdanes: Scope and limitations: Synthesis of isofregenedane type tetrahydronaphthalenic diterpenes . Tetrahedron 2003 , 59 , 2333 – 2343 .
   Web of Science ®Google Scholar
• Vlad , P. F. ; Gorincioi , E. K. ; Coltsa , M. N. Synthesis of 5,6-dehydro-7-oxoisodrimenin from drim-8-en-7-one . Russ. Chem. Bull. 2003 , 2 , 502 – 504 .
   Google Scholar
• Vlad , P. F. ; Popa , D. P. ; Gorincioi , E. K. ; Coltsa , M. N. ; Mironov , G. N. Synthesis of 11-hydroxydrim-8(9)-en-7-one, 11,12-dihydroxydrim-8(9)-en-7-one from drim-8(9)-en-7-one . Russ. Chem. Bull. 2000 , 49 , 98 – 101 .
   Web of Science ®Google Scholar
• CrysAlis RED, Oxford Diffraction Ltd., version 1.171.34.76, 2003.
   Google Scholar
• Sheldrick , G. M. A short history of SHELX . Acta Crystallogr. 2008 , A64 , 112 – 122 .
   Web of Science ®Google Scholar
• Sugamoto , K. , Matsusita , Y. , Matsui , K. , Kurogi , C. , Matsui , T. Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei . Tetrahedron. 2011 , 67 , 5346 – 5359 .
   Web of Science ®Google Scholar
• National Committee on Clinical Laboratory Standards (NCCLS). Antimicrobial Susceptibility Standards (ATS) 2003, for M7 (CMI) and M100.
   Google Scholar