Facile and Simple Synthesis of Ring C Aromatic Diterpenes: Synthesis of (+)-13-Hydroxypodocarpa-8,11,13-triene and (+)-7-Deoxynimbidiol

REFERENCES

• Nakano , T. In Studies in Natural Products Chemistry ; Atta-ur-Rahman (Ed.); Elsevier Science : Amsterdam , 1989 ; vol. 4 , pp. 403 – 429 , and references cited therein .
   Google Scholar
• (a) Dellar , J. E. ; Cole , M. D. ; Waterman , P. G. Antimicrobial abietane diterpenoids from Plectranthus elegans . Phytochemistry 1996 , 41 , 735 – 738 ; (b) Batista , O. ; Simoes , F. ; Duarte , A. ; Valdeira , M. L. ; de la Torre , M. ; Rodriguez , B. An antimicrobial abietane from the root of Plectranthus hereroensis . Phytochemistry 1995 , 38 , 167 – 169 ; (c) Nakatani , N. ; Inatani , R. Constituents of spices of the family Labiatae, part III: Two antioxidative diterpenes from rosemary (Rosmarinus officinalis L.) and a revised structure for rosmanol . Agric. Biol. Chem. 1984 , 48 , 2081 ; (d) Achenbach , H. ; Waibel , R. ; Nkunya , M. H. H. ; Weenen , H. Antimalarial compounds from Hoslundia opposita . Phytochemistry 1992 , 31 , 3781 – 3784 ; (e) Gao , J. ; Han , G. Cytotoxic abietane diterpenoids from Caryopteris incana . Phytochemistry 1997 , 44 , 759 – 761 .
   PubMed Web of Science ®Google Scholar
• Kuo , Y.-H. ; Chang , Ch.-I. ; Lee , Ch.-K. Six podocarpane-type trinorditerpenes from the bark of Taiwania cryptomerioides . Chem. Pharm. Bull. 2000 , 48 , 597 – 599 .
   PubMedGoogle Scholar
• Xiong , Y. ; Wang , K. ; Pan , Y. ; Sun , H. ; Tu , J. Isolation, synthesis, and anti-tumor activities of a novel class of podocarpic diterpenes . Bioorg. Med. Chem. Lett. 2006 , 16 , 786 – 789 .
   PubMed Web of Science ®Google Scholar
• (a) Sutherland , J. K. Polyene cyclizations. In Comprehensive Organic Synthesis ; B. M. Trost and I. Fleming (Eds.); Pergamon Press : Oxford , 1991; vol. 3, pp. 341–377; (b) Harring , S. R. ; Livinghouse , T. Polyene cascade cyclizations mediated by BF3 · CH3NO2: An unusually efficient method for the direct, stereospecific synthesis of polycyclic intermediates via cationic initiation at non-functionalized 3 alkenes: An application to the total synthesis of (±)-taxodione. Tetrahedron 1994, 50, 9229–9254; (c) Burnell , R. H. ; Caron , S. Approach to the synthesis of candelabrone and synthesis of 3,7-diketo-12-hydroxyabieta-8,11,13-triene. Can. J. Chem. 1992, 70, 1446-1454; (d) Tada , M. ; Nishiiri , S. ; Zhixiang , Y. ; Imai , Y. ; Tajima , S. ; Okazaki , N. ; Kitano , Y. ; Chiba , K. Synthesis of (+)- and (−)-ferruginol via asymmetric cyclization of a polyene. J. Chem. Soc., Perkin Trans. 1 2000, 2657–2664; (e) Ishihara , K. ; Ishibashi , H. ; Yamamoto , H. Enantioselective biomimetic cyclization of homo(polyprenyl)arenes: A new entry to (+)-podpcarpa-8,11,13-triene diterpenoids and (−)-tetracyclic polyprenoid of sedimentary origin. J. Am. Chem. Soc. 2001, 123, 1505–1506; (f) Ishihara , K. ; Ishibashi , H. ; Yamamoto , H. Enantio- and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs: A new entry to (−)-ambrox, (+)-podocarpa-8,11,13-triene diterpenoids, and (−)-tetracyclic polyprenoid of sedimentary origin. J. Am. Chem. Soc. 2002, 124, 3647–3655; (g) Majetich , G. ; Liu , S. ; Fang , J. ; Siesel , D. ; Zhang , Y. Use of conjugated dienones in cycloalkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (±)-hinokione, (±)-nimbidiol, sageone, and miltirone. J. Org. Chem. 1997, 62, 6928–6951.
   Google Scholar
• (a) Nakano , T. ; Villamizar , J. ; Maillo , M. A. Synthesis of drimanic sesquiterpenes, (+)-valdiviolide, (+)-12α-hydroxyisodrimenin, and (+)-winterin . J. Chem. Res. Synop. 1998 , 560 – 561 ; (b) Nakano , T. ; Villamizar , J. ; Maillo , M. A. A new entry to (+)-albicanol and (+)-bicyclofarnesol . J. Chem. Res. Synop. 1995 , 330 – 331 .
   Google Scholar
• (a) Nakano , T. ; Alonso , R. ; Maillo , M. A. ; Martin , A. ; Nunez , R. A. A facile access to optically active ring C aromatic diterpene derivatives: Highly efficient synthesis of (+)-12-methyl-7-oxopodocarpa-8,11,13-triene-13-carboxylic acid and (+)-13-methyl-7-oxopodocarpa-8,11,13-triene-12-carboxylic acid from manool . Tetrahedron Lett. 1995 , 36 , 3801 – 3804 ; (b) Nakano , T. ; Alonso , R. ; Maillo , M. A. ; Martin , A. ; Nunez , R. A. Facile access to optically active ring C aromatic diterpene derivatives from manool: Highly efficient syntheses of (+)-12-methyl-7-oxopodocarpa-8,11,13-triene-13-carboxylic acid, (+)-13-methyl-7-oxopodocarpa-8,11,13-triene-12-carboxylic acid, and (+)-nimbiol . J. Chem. Soc., Perkin Trans. 1 , 1998 , 1423 – 1426 .
   Google Scholar
• (a) Villamizar , J. ; Fuentes , J. ; Salazar , F. ; Tropper , E. ; Alonso , R. Facile access to optically active labdane-type diterpenes from (+)-manool: Synthesis of (+)-coronarin E, (+)-15,16-epoxy-8(17),13(16),14-labdatriene, and (+)-labda-8(17),13(Z)-diene-15,16-diol . J. Nat. Prod. 2003 , 66 , 1623 – 1627 ; (b) Villamizar , J. ; Orcajo , A. L. ; Fuentes , J. ; Tropper , E. ; Alonso , R. Highly efficient synthesis of optically active sesquiterpene hydroquinone (+)-zonarol and sesquiterpene quinone (+)-zonarone . J. Chem. Res. Synop. 2002 , 395 – 397 ; (c) Villamizar , J. E. ; Juncosa , J. ; Pittelaud , J. ; Hernandez , M. ; Canudas , N. ; Tropper , E. ; Salazar , F. ; Fuentes , J. Facile access to labdane-type diterpenes: Synthesis of coronarin C, zerumin B, labda-8(17),13(14)-dien-15,16-olide, and derivatives from (+)-manool . J. Chem. Res. 2007 , 342 – 346 .
   PubMed Web of Science ®Google Scholar
• Zambrano , J. L. ; Rosales , V. ; Nakano , T. First formal synthesis of (+)-nimbidiol: Synthesis, x-ray structure, and anticancer activity of a novel ring C aromatic diterpene: Dimethyl (+)-podocarpa-8,11,13-triene-12,13-dicarboxylate . Tetrahedron Lett. 2003 , 44 , 1859 – 1862 .
   Google Scholar
• Alvarez-Manzaneda , E. ; Chahboun , R. ; Cabrera , E. ; Alvarez , E. ; Alvarez-Manzaneda , R. ; Hmamouchi , M. ; Es-Samti , H. Novel synthetic strategy toward abietane and podocarpane-type diterpenes from (−)-sclareol: Synthesis of the antitumor (+)-7-deoxynimbidiol . Tetrahedron Lett. 2007 , 48 , 8930 – 8934 .
   Web of Science ®Google Scholar
• Alvarez-Manzaneda Roldan , E. ; Santiago , J. L. R. ; Chahboun , R. A new route toward 7-oxo-13-hydroxy-8,11,13-podocarpatrienes from labdane diterpenes . J. Nat. Prod. 2006 , 69 , 563 – 566 .
   PubMedGoogle Scholar
• Nakano , T. ; Maillo , M. A. Total synthesis of (−)-jolkinolide E, the enantiomer of the natural substance . J. Chem. Res. 1985 , 268 – 269 .
   Google Scholar
• do Ceu Costa , M. ; Tavares , R. ; Motherwell , W. B. ; Joao , M. ; Curto , M. Novel diastereoselective routes for the synthesis of the ambergris ketals. Tetrahedron Lett. 1994, 35, 8839–8842.
   Google Scholar
• Wu , H. ; Nakamura , H. ; Kobayashi , J. ; Kobayashi , M. ; Ohizumi , Y. ; Hirata , Y. Physiologically active marine natural products from Porifera, XII: Structures of agelasines, diterpenes having a 9-methyladeninium chromophore isolated from the Okinawan marine sponge Agelas nakamurai Hoshino . Bull. Chem. Soc. Jpn. 1986 , 59 , 2495 – 2504 .
   Web of Science ®Google Scholar
• Miyake , T. ; Kigoshi , H. ; Akita , H. Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D . Tetrahedron: Asymmetry 2007 , 18 , 2915 – 2922 .
   Web of Science ®Google Scholar
• Demir , A. S. ; Emrullahoglu , M. Manganese(III) acetate: A versatile reagent in organic chemistry . Curr. Org. Synth. 2007 , 4 ( 3 ), 321 – 351 .
   Google Scholar