New synthesis of nematocidal natural products dithiocynates thiocyanatin A and 1,8,16-trihydroxyhexadecane

Refercences

• Bandgar , BP , Sadavarte , VS and Uppalla , LS . 2000 . Selective and rapid oxidation of primary, allylic and benzylic alcohols to the corresponding carbonyl compounds with NaNO2-acetic anhydride under mild and solvent-free conditions . Journal of Chemical Society, Perkin Transactions , 1 : 3359 – 3560 .
   Google Scholar
• Caldicott , AB , Simoneit , BRT and Eglinton , G . 1975 . Gas chromatographic mass spectrometric studies of long chain hydroxyl acids 5. Alkanetriols in psylatophyte . Phytochemistry , 14 : 2223 – 2228 .
   Web of Science ®Google Scholar
• Capon , RJ , Skene , C , Liu , EH-T , Lacey , E , Gill , JH Heiland , K . 2004 . Nematocidal thiocyanatins from a southern Australian marine sponge Oceanapia sp . Journal of Natural Products , 67 : 1277 – 1282 .
   PubMed Web of Science ®Google Scholar
• Capon , RJ , Skene , C , Liu , EH-T , Lacey , E , Gill , JH Heiland , K . 2001 . The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge Oceanapia sp . Journal of Organic Chemistry , 66 : 7765 – 7769 .
   PubMed Web of Science ®Google Scholar
• Fusetani , N , Wolstenholme , HJ , Shinoda , K , Asai , N , Matsunaga , S Onuki , H . 1992 . Bioactive marine metabolites 44. Two sesquiterpene isocyanides and a sesquiterpene thiocyanate from the marine sponge Acanthella cf. cavernosa and the nudibranch Phyllidia ocellata . Tetrahedron Letters , 33 : 6823 – 6826 .
   Web of Science ®Google Scholar
• Gupta , N , Sonu, Kad , GL and Singh , J . 2007 . Acidic ionic liquid [bmim]HSO4: An efficient catalyst for thioacetalization of carbonyl compounds and their subsequent deprotection . Catalysis Communications , 8 : 1323 – 1328 .
   Web of Science ®Google Scholar
• He , HY , Faulkner , DJ , Shumsky , JS , Hong , K and Clardy , J . 1989 . A sesquiterpene thiocyanate and three sesquiterpene isothiocyanates from the sponge Trachyopsis aplysinoides . Journal of Organic Chemistry , 54 : 2511 – 2514 .
   Web of Science ®Google Scholar
• He , HY , Salva , J , Catalos , RF and Faulkner , DJ . 1992 . Sesquiterpene thiocyanates and isothiocyanates from axinyssa aplysinoides . Journal of Organic Chemistry , 57 : 3191 – 3194 .
   Web of Science ®Google Scholar
• Iranpoor , N , Firouzabadi , H and Shaterian , HR . 2005 . Efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding thiocyanates with in situ-generated Ph3P(SCN)2 . Phosphorus, Sulphur and Silicon and the Related Elements , 180 : 2093 – 2096 .
   Web of Science ®Google Scholar
• Kad , GL , Kaur , I , Bhandari , M , Singh , J and Kaur , J . 2003 . Functional group transformation of diols, cyclic ethers, and lactones using aqueous hydrobromic acid and phase transfer catalyst under microwave irradiation . Organic Process Research & Development , 7 : 339 – 340 .
   Web of Science ®Google Scholar
• Kad , GL , Kaur , J , Bansal , P and Singh , J . 1996 . Selective iodination of benzylic alcohols with sodium iodide over KSF-clay under microwave irradiation . Journal of Chemical Research (S) , : 188 – 189 .
   Web of Science ®Google Scholar
• Kad , GL , Singh , V , Kaur , KP and Singh , J . 1997 . Selective preparation of benzylic bromides in dry media coupled with microwave irradiation . Tetrahedron Letters , 38 : 1079 – 1080 .
   Web of Science ®Google Scholar
• Kochi , JK and Tamura , M . 1971 . Mechanism of the silver-catalyzed reaction of grignard reagents with alkyl halides . Journal of American Chemical Society , 93 : 1483 – 1485 .
   Web of Science ®Google Scholar
• Okino , T , Yoshimura , E , Hirota , H and Fusetani , N . 1996 . New antifouling sesquiterpenes from four nudibranchs of the family phyllidiidae . Tetrahedron , 52 : 9447 – 9454 .
   Web of Science ®Google Scholar
• Pham , AT , Ichiba , T , Yoshida , WY , Scheuer , PJ , Uchida , T Tanaka , J . 1991 . Two marine sesquiterpene thiocyanates . Tetrahedron Letters , 32 : 4843 – 4846 .
   Web of Science ®Google Scholar
• Simpson , JS , Garson , MJ , Hopper , JNA , Cline , EI and Angerhofer , CK . 1997 . Terpene metabolites from the tropical marine sponge Axinyssa sp. nov . Australian Journal of Chemistry , 50 : 1123 – 1127 .
   Web of Science ®Google Scholar
• Simpson , JS and Garson , MJ . 1998 . Thiocyanate biosynthesis in the tropical marine sponge Axinyssan sp . Tetrahedron Letters , 39 : 5819 – 5822 .
   Web of Science ®Google Scholar
• Singh , A , Sharma , ML and Singh , J . 2008 . First synthesis of antitubercular natural product 2-hydroxy-5-(4-hydroxy-benzyl) benzaldehyde (Forkienin) . Journal of Chemical Research , : 148 – 149 .
   Web of Science ®Google Scholar
• Singh , J , Sharma , M , Kad , GL and Chhabra , BR . 1997 . Selective oxidation of allylic methyl groups over a solid support under microwave irradiation . Journal of Chemical Research (S) , : 264 – 265 .
   Web of Science ®Google Scholar
• Singh , J , Gupta , N , Kad , GL and Kaur , J . 2006 . Efficient role of ionic liquid (bmim)HSO4 as novel catalyst for monotetrahydropyranylation of diols and tetrahydropyranylation of alcohols . Synthetic Communications , 36 : 2893 – 2900 .
   Web of Science ®Google Scholar