Four- and Eight-Carbon Homologation of Benzaldehyde by (1Z,3Z)-Butyltelluro-1,3-Butadiene: Synthesis of Navenone B: Alarm Pheromone of the Mollusk Navanax inermis

REFERENCES

• Hardie , J. ; Minks , A. K. In Pheromones of Non-lepidopteran Insects Associated with Agricultural Plants ; CABI Publishing : New York , 1999 ; pp. 69 – 89 .
   Google Scholar
• (a) Nicolau , K. C. ; Ramphal , J. Y. ; Petasis , N. A. ; Serhan , C. N. Lipoxins and related eicosanoids: Biosynthesis, biological properties, and chemical synthesis. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100–1116; (b) Serhan , C. N. Lipoxin biosynthesis and its impact in inflammatory and vascular events. Biochim. Biophys. Acta 1994, 1212, 1–25; (c) Serhan , C. N. Lipoxins and novel aspirin-triggered 15-epi-lipoxins (ATL): A jungle of cell-cell interactions or a therapeutic opportunity? Prostaglandins 1997, 53, 107–137; (d) Serhan , C. N. Lipoxins and aspirin-triggered 15-epi-lipoxin biosynthesis: An update and role in anti-inflammation and pro-resolution. Prostaglandins & Other Lipid Mediat . 2002, 68–69, 433–435.
   Web of Science ®Google Scholar
• (a) Woerlee , E. F. G. ; Bosma , R. H. A. ; Van Eijl , J. M. M. ; Mol , J. C. Metathesis of conjugated dienes: A possible way to synthesize insect pheromones and other speciality chemicals . Appli. Catal. 1984 , 10 , 219 – 229 ; (b) Bartelt , R. J. ; Weisleder , D. ; Plattner , R. Synthesis of nitidulid beetle pheromones: Alkyl-branched tetraene hydrocarbons . J. Agric. Food Chem. 1990 , 38 , 2192 – 2196 ; (c) Crousse , B. ; Alami , M. ; Linstrumelle , G. A. stereocontrolled method for the synthesis of conjugated polyenes . Tetrahedron Lett. 1995 , 36 , 4245 – 4248 ; (d) Alami , M. ; Crousse , B. ; Linstrumelle , G. ; Mambu , L. ; Larchevêque , M. A versatile to conjugated hydroxy (E,Z,E,E)-tetraenoic acids: Highly chemo- and stereoselective synthesis of lipoxin B4 . Tetrahedron: Asymmetry 1997 , 17 , 2949 – 2958 ; (e) Crousse , B. ; Alami , M. ; Linstrumelle , G. Stereocontrolled synthesis of (E,E,E)-chlorotrienes: Efficient intermediates for the construction of all E conjugated polyenes . Tetrahedron Lett. 1997 , 38 , 5297 – 5300 ; (f) Solladié , G. ; Kalaï , C. ; Adamy , M. ; Colobert , F. Stereoselective synthesis of conjugated all-trans-tetraenes: Application to the synthesis of β-parinaric acid methyl ester . Tetrahedron Lett. 1997 , 38 , 6917 – 6920 .
   Google Scholar
• Petasis , N. A. ; Akritopoulou-Zanze , I. ; Fokin , W. ; Bernasconi , G. ; Keledjian , R. ; Yang , R. ; Uddin , J. ; Nagulapalli , K. C. ; Serhan , C. N. Design, synthesis, and bioactions of novel stable mimetics of lipoxins and aspirin-triggered lipoxins . Prostaglandins, Leukotrienes Essential Fatty Acids 2005 , 73 , 301 – 321 , and references therein .
   PubMed Web of Science ®Google Scholar
• (a) Maeta , H. ; Suzuki , K. Two- and four-carbon homologation of aldehyde by AgClO4-catalyzed addition of alkoxyalkenylzirconocene chloride . Tetrahedron Lett. 1993 , 34 , 341 – 344 ; (b) Petroski , R. J. ; Bartelt , R. J. New phosphonate reagents for aldehyde homologation . Synth. Commun. 2007 , 37 , 3841 – 3854 , and references therein ; (c) Petroski , R. J. ; Bartelt , R. J. Direct aldehyde homologation utilized to construct a conjugated-tetraene hydrocarbon insect pheromone . J. Agric. Food Chem. 2007 , 55 , 2282 – 2287 ; (5d) Wollenberg , R. H. Efficient conversion of carbonyl compounds to conjugated dienals . Tetrahedron Lett. 1978 , 8 , 717 – 720 .
   Web of Science ®Google Scholar
• (a) Crousse , B. ; Mladenova , M. ; Ducept , P. ; Alami , M. ; Linstrumelle , G. Stereoselective approaches to (E,E,E) and (Z,E,E)-α-chloro-ω-substituted hexatrienes: Synthesis of all E polyenes . Tetrahedron 1999 , 55 , 4353 – 4368 ; (b) Hemming , K. ; Taylor , R. J. K. A new route to trienals using 2-substituted 2H-pyran-based Wittig reagents . J. Chem. Soc. Comm. 1993 , 1409 – 1410 ; (c) Soullez , D. ; Ramondenc , Y. ; Pie , G. ; Duhamel , L. Alarm pheromones, navenones A, B, and C (1a–c) are synthesized in a one-pot reaction by the means of a powerful polyvinylogation reagent, the 6-lithio-1-methoxyhexa-1,3,5-triene 3 . Nat. Prod. Lett. 1994 , 4 , 203 – 208 ; (d) Solladié , G. ; Colobert , F. ; Stone , G. B. A short and easy route to conjugated all-e-trienes and tetraenes: Application to the synthesis of navenone B and lignarenone B . Synlett 1995 , 1135 – 1137 ; (e) Solladié , G. ; Somny , F. ; Colobert , F. Enantioselective synthesis of haminol-1, an alarm pheromone of a mediterranean mollusc . Tetrahedron: Asymmetry 1997 , 8 , 801 – 810 .
   Web of Science ®Google Scholar
• Dabdoub , M. J. ; Dabdoub , V. B. ; Guerrero , P. G. ; Silveira , C. C. (1Z,3Z)-Buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1Z, 3Z)-butyltelluro-1,3-butadienes and (1Z,3Z)-1,4-bis(butyltelluro)-1,3-butadienes . Tetrahedron 1997 , 53 , 4199 – 4218 .
   Web of Science ®Google Scholar
• Petragnani , N. Tellurium in Organic Synthesis; Best Synthetic Methods ; Academic Press : London , 1994 .
   Google Scholar
• (a) Barros , S. M. ; Dabdoub , M. J. ; Dabdoub , V. B. , Comasseto , J. V. Hydrotelluration of acetylenes: Synthesis of vinylic tellurides, divinyl tellurides, and 1-(organyltelluro)-1,3-butadienes. Organometallics 1989, 8, 1661–1665; (b) Dabdoub , M. J. ; Cassol , T. M. Total control on the synthesis of regio and stereoisomers of vinylic tellurides. Tetrahedron 1995, 51, 12971–12982.
   Web of Science ®Google Scholar
• (a) Dabdoub , M. J. ; Dabdoub , V. B. ; Comasseto , J. V. Synthesis of (E)-1,4-bis(organyl) but-1-en-3-ynes by lithlium–tellurium exchange reaction on (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes . Tetrahedron Lett. 1992 , 33 , 2261 – 2264 ; (b) Tucci , F. C. ; Chieffi , A. ; Comasseto , J. V. ; Marino , J. P. Tellurium in organic synthesis: Preparation of Z-vinylic cuprates from Z-vinylic tellurides and their reaction with enones and epoxides . J. Org. Chem. 1996 , 61 , 4975 – 4989 .
   Web of Science ®Google Scholar
• Dabdoub , M. J. ; Dabdoub , V. B. ; Baroni , A. C. M. ; Hurtado , G. R. ; Barbosa , S. L. Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z, 3Z)-butyltelluro-4-methoxy-1,3-butadiene . Tetrahedron Lett. 2010 , 51 , 1666 – 1670 .
   Web of Science ®Google Scholar
• Sleeper , H. L. ; Fenical , W. Navenones A–C: Trail-breaking alarm pheromones from the marine opisthobranch Navanax inermis . J. Am. Chem. Soc. 1977 , 99 , 2367 – 2368 .
   PubMed Web of Science ®Google Scholar
• Shono , T. ; Hayata , Y. ; Tsubouchi , A. ; Takeda , T. Formation of conjugated dienes by the reaction of titanocene alkenylidene complexes with alkynes . Tetrahedron Lett. 2006 , 47 , 1257 – 1260 .
   Web of Science ®Google Scholar
• (a) Furber , M. ; Taylor , R. J. K. Stereospecific synthesis of dienes and trienes from pyrylium perchlorate: A convergent approach to leukotrienes . J. Chem. Soc., Chem. Commun. 1985 , 782 – 783 ; (b) Furber , M. ; Herbert , J. M. ; Taylor , R. J. K. Stereoselective synthesis of 2Z,4E-dienals by addition of organometallic reagents to pyrylium perchlorate . J. Chem. Soc., Perkin Trans. 1 1989 , 683 – 690 ; (c) Borer , B. C. ; Taylor , R. J. K. The chemical structure of leukotriene B4: Lignarenone A and B . J. Chem. Res. 1990 , 162 .
   Google Scholar
• (a) De Medeiros , E. F. ; Herbert , J. M. ; Taylor , R. J. K. The synthesis and absolute configuration of the novel ichthyotoxic diacylglycerol, umbraculumin A . Tetrahedron Lett. 1990 , 31 , 5843 – 5844 ; (b) De Medeiros , E. F. ; Herbert , J. M. ; Taylor , R. J. K. The synthesis and absolute configuration of the novel ichthyotoxic diacyiglycerols, umbraculumin A, and umbraculumin C . J. Chem. Soc., Perkin Trans. 1 1991 , 2725 – 2730 .
   Web of Science ®Google Scholar
• Borer , B. C. ; Taylor , R. J. K. Synthesis of (+)-leukotriene B4 (LTB4) methyl ester and (-)-(5 R)-LTB4 methyl ester via pyrylium methodology . Synlett 1992 , 2 , 117 – 118 , and references therein .
   Google Scholar
• Hemming , K. ; Taylor , R. J. K. A new route to trienals using 2-substituted 2H-pyran-based Wittig reagents . J. Chem. Soc., Chem. Commun. 1993 , 1409 – 1410 .
   Google Scholar
• Taylor , R. J. K. ; Hemming , K. ; De Medeiros , E. F. Pyrylium salts in polyene natural product synthesis: Organometallic additions to 4-methylpyrylium tetrafluoroborate . J. Chem. Soc., Perkin Trans. 1 1995 , 2385 – 2392 .
   Google Scholar
• Baeckström , P. ; Jacobsson , U. ; Norin , T. ; Unelius , C. R. Synthesis and characterization of all four isomers of methyl 2,4-decadienoate for an investigation of the pheromone components of Pityogenes chaicographus . Tetrahedron 1988 , 44 , 2541 – 2548 .
   Web of Science ®Google Scholar
• Cava , M. P. ; Engman , L. Organotellurium compounds: A convenient synthesis of some aliphatic ditellurides . Synth. Commun. 1982 , 12 , 163 – 165 .
   Web of Science ®Google Scholar