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Volumn 37, Issue 6, 2004, Pages 365-377

Evolution of dithiane-based strategies for the construction of architecturally complex natural products

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIANE LINCHPIN; 13 DEOXYTEDANOLIDE; ALDEHYDE; ALKENE; ANION; CALYCULIN A; CALYCULIN B; DITHIANE; EPOXIDE; HALIDE; KETONE; MYCOTICIN; NATURAL PRODUCT; ORGANIC COMPOUND; RIMOCIDINOLIDE; SILOXANE; SPONGISTATIN 1; SPONGISTATIN 2; TEDANOLIDE; TSUKUBAENOLIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 2942637483     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030245r     Document Type: Review
Times cited : (295)

References (85)
  • 1
    • 0037925733 scopus 로고
    • Phenanthrensynthesen über intraionische Isomerisationen
    • Wittig, G.; Davis, P.; Koenig, G. Phenanthrensynthesen über intraionische Isomerisationen. Chem. Ber. 1951, 84, 627-631.
    • (1951) Chem. Ber. , vol.84 , pp. 627-631
    • Wittig, G.1    Davis, P.2    Koenig, G.3
  • 2
    • 0002692198 scopus 로고
    • Umpolung (dipole inversion) of carbonyl reactivity
    • Seebach, D.; Kolb, M. Umpolung (dipole inversion) of carbonyl reactivity. Chem. Ind. 1974, 7, 687-692.
    • (1974) Chem. Ind. , vol.7 , pp. 687-692
    • Seebach, D.1    Kolb, M.2
  • 3
    • 0018454939 scopus 로고
    • Methods of reactivity umpolung
    • Seebach, D. Methods of Reactivity Umpolung. Angew. Chem., Int. Ed. Engl. 1979, 18, 239-336.
    • (1979) Angew. Chem., Int. Ed. Engl. , vol.18 , pp. 239-336
    • Seebach, D.1
  • 4
    • 33748737077 scopus 로고
    • Carbanions of 1,3-Dithianes. Reagents for C-C bond formation by nucleophilic displacement and carbonyl addition
    • Corey, E. J.; Seebach, D. Carbanions of 1,3-Dithianes. Reagents for C-C Bond Formation by Nucleophilic Displacement and Carbonyl Addition. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075-1077.
    • (1965) Angew. Chem., Int. Ed. Engl. , vol.4 , pp. 1075-1077
    • Corey, E.J.1    Seebach, D.2
  • 5
    • 0000445823 scopus 로고
    • Synthesis of 1,n-dicarbonyl derivates using carbanions from 1,3-dithianes
    • Corey, E. J.; Seebach, D. Synthesis of 1,n-Dicarbonyl Derivates Using Carbanions from 1,3-Dithianes. Angew. Chem., Int. Ed. Engl. 1965, 4, 1077-1078.
    • (1965) Angew. Chem., Int. Ed. Engl. , vol.4 , pp. 1077-1078
    • Corey, E.J.1    Seebach, D.2
  • 6
    • 0043206066 scopus 로고    scopus 로고
    • The role of 1,3-dithianes in natural product synthesis
    • For a review and selected examples of natural product construction via dithiane-based strategies, see: (a) Yus, M.; Najera, C.; Foubelo, F. The role of 1,3-dithianes in natural product synthesis. Tetrahedron 2003, 59, 6147-6212.
    • (2003) Tetrahedron , vol.59 , pp. 6147-6212
    • Yus, M.1    Najera, C.2    Foubelo, F.3
  • 8
    • 0023204667 scopus 로고
    • Total synthesis of debromoaplysiatoxin and aplysiatoxin
    • (c) Park, P. U.; Broka, C. A.; Johnson, B. F.; Kishi, Y. Total Synthesis of Debromoaplysiatoxin and Aplysiatoxin. J. Am. Chem. Soc. 1987, 109, 6205-6207.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6205-6207
    • Park, P.U.1    Broka, C.A.2    Johnson, B.F.3    Kishi, Y.4
  • 9
    • 0023625805 scopus 로고
    • Total synthesis of (+)-gloeosporone: Assignment of absolute configuration
    • (d) Adam, G.; Zibuck, R.; Seebach, D. Total Synthesis of (+)-Gloeosporone: Assignment of Absolute Configuration. J. Am. Chem. Soc. 1987, 109, 6176-6177.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6176-6177
    • Adam, G.1    Zibuck, R.2    Seebach, D.3
  • 10
    • 0000237762 scopus 로고
    • Oxidative hydrolysis of 1,3-dithiane derivatives to carbonyl compounds using n-halosuccinimide reagents
    • (a) Corey, E. J.; Erickson B. W. Oxidative Hydrolysis of 1,3-Dithiane Derivatives to Carbonyl Compounds Using N-Halosuccinimide Reagents. J. Org. Chem. 1971, 36, 3553-3560.
    • (1971) J. Org. Chem. , vol.36 , pp. 3553-3560
    • Corey, E.J.1    Erickson, B.W.2
  • 12
    • 84989423687 scopus 로고
    • Umpolung of the reactivity of carbonyl compounds through sulfur-containing reagents
    • (c) Grobel, B.-T.; Seebach, D. Umpolung of the Reactivity of Carbonyl Compounds Through Sulfur-Containing Reagents. Synthesis 1977, 357-402.
    • (1977) Synthesis , pp. 357-402
    • Grobel, B.-T.1    Seebach, D.2
  • 13
    • 0001144019 scopus 로고
    • A simple method for dethioacetalization
    • (d) Stork, G.; Zhao, K. A Simple Method for Dethioacetalization. Tetrahedron Lett. 1989, 30, 287-290.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 287-290
    • Stork, G.1    Zhao, K.2
  • 17
    • 0024390379 scopus 로고
    • Total synthesis of (+)-hydroxyjatrophone A and (+)-hydroxyjatrophone B
    • (c) Smith, A. B., III; Lupo, A. T.; Ohba, M.; Chen, K.; Total Synthesis of (+)-Hydroxyjatrophone A and (+)-Hydroxyjatrophone B. J. Am. Chem. Soc. 1989, 111, 6648-6656.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6648-6656
    • Smith III, A.B.1    Lupo, A.T.2    Ohba, M.3    Chen, K.4
  • 18
    • 2942660272 scopus 로고    scopus 로고
    • note
    • The synthesis of the unnatural congener, (+)-normethyljatrophone, was achieved initially; see ref 8b. (diagram presented)
  • 20
    • 0001232687 scopus 로고
    • Thermal racemization of allylic sulfoxides and interconversion of allylic sulfoxides and sulfenates. Mechanism and stereochemistry
    • (a) Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. Thermal Racemization of Allylic Sulfoxides and Interconversion of Allylic Sulfoxides and Sulfenates. Mechanism and Stereochemistry. J. Am. Chem. Soc. 1968, 90, 4869-4876.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 4869-4876
    • Bickart, P.1    Carson, F.W.2    Jacobus, J.3    Miller, E.G.4    Mislow, K.5
  • 21
    • 0009276253 scopus 로고
    • Allylic sulfoxides. Useful intermediates in organic synthesis
    • (b) Evans, D. A.; Andrews, G. C. Allylic Sulfoxides. Useful Intermediates in Organic Synthesis. Acc. Chem. Res. 1974, 7, 147-155.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 147-155
    • Evans, D.A.1    Andrews, G.C.2
  • 22
    • 33847804804 scopus 로고
    • New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride
    • Mukaiyama, T.; Banno, K.; Naraska, K. New Cross-Aldol Reactions. Reactions of Silyl Enol Ethers with Carbonyl Compounds Activated by Titanium Tetrachloride. J. Am. Chem. Soc. 1974, 96, 7503-7509.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7503-7509
    • Mukaiyama, T.1    Banno, K.2    Naraska, K.3
  • 25
    • 0018642843 scopus 로고
    • Synthesis of macrocycles by intramolecular ketophosphonate reactions
    • (a) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R.; Petasis, N. A. Synthesis of Macrocycles by Intramolecular Ketophosphonate Reactions. J. Org. Chem. 1979, 44, 4011-4013.
    • (1979) J. Org. Chem. , vol.44 , pp. 4011-4013
    • Nicolaou, K.C.1    Seitz, S.P.2    Pavia, M.R.3    Petasis, N.A.4
  • 26
    • 33645374504 scopus 로고
    • Large-ring lactones by internal ketophosphonate cyclizations
    • (b) Stork, G.; Nakamura, E. Large-ring Lactones by Internal Ketophosphonate Cyclizations. J. Org. Chem. 1979, 44, 4010-4011.
    • (1979) J. Org. Chem. , vol.44 , pp. 4010-4011
    • Stork, G.1    Nakamura, E.2
  • 27
    • 0038219364 scopus 로고
    • A simple and convenient method for the cleavage of dithioacetals to the corresponding carbonyl compounds
    • After our work, Cossy has published a modification of these conditions: Cossy, J. A Simple and Convenient Method for the Cleavage of Dithioacetals to the Corresponding Carbonyl Compounds. Synthesis 1987, 1113-1115.
    • (1987) Synthesis , pp. 1113-1115
    • Cossy, J.1
  • 28
    • 0023245677 scopus 로고
    • FK-506, a novel immunosuppressant isolated from A streptomyces I. Fermentation, isolation, and physicochemical and biological characteristics
    • Kino, T.; Hatanaka, H.; Hashimoto, M.; Nishiyama, M.; Goto, T.; Okuhara, M.; Kohsaka, M.; Aoki, H.; Imanaka, H. FK-506, A Novel Immunosuppressant Isolated From A Streptomyces I. Fermentation, Isolation, and Physicochemical and Biological Characteristics. J. Antibiot. 1987, 40, 1249-1255.
    • (1987) J. Antibiot. , vol.40 , pp. 1249-1255
    • Kino, T.1    Hatanaka, H.2    Hashimoto, M.3    Nishiyama, M.4    Goto, T.5    Okuhara, M.6    Kohsaka, M.7    Aoki, H.8    Imanaka, H.9
  • 29
    • 0028338336 scopus 로고
    • Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic
    • Smith, A. B., III; Chen, K.; Robinson, D. J.; Laasko, L. M.; Hale, K. J. Formal Total Synthesis of FK506. Concise Construction of the C(10)-C(34) Segment via an Effective Coupling Tactic. Tetrahedron Lett. 1994, 35, 4271-4274.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4271-4274
    • Smith III, A.B.1    Chen, K.2    Robinson, D.J.3    Laasko, L.M.4    Hale, K.J.5
  • 30
    • 0016724057 scopus 로고
    • Rapamycin (AY-22,989), a new antifungal antibiotic I. Taxonomy of the producing streptomycete and isolation of the active principle
    • Vézina, C.; Kudelski, A.; Sehgal, S. N. Rapamycin (AY-22,989), A New Antifungal Antibiotic I. Taxonomy of the Producing Streptomycete and Isolation of the Active Principle. J. Antibiot. 1975, 28, 721-726.
    • (1975) J. Antibiot. , vol.28 , pp. 721-726
    • Vézina, C.1    Kudelski, A.2    Sehgal, S.N.3
  • 31
    • 0031018562 scopus 로고    scopus 로고
    • A unified total synthesis of the immunomodulators (-)-rapamycin and (-)-27-demethoxyrapamycin: Construction of the C(21-42) perimeters
    • (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. J., Jr. A Unified Total Synthesis of the Immunomodulators (-)-Rapamycin and (-)-27-Demethoxyrapamycin: Construction of the C(21-42) Perimeters. J. Am. Chem. Soc. 1997, 119, 947-961.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 947-961
    • Smith III, A.B.1    Condon, S.M.2    McCauley, J.A.3    Leazer Jr., J.L.4    Leahy, J.W.5    Maleczka Jr., R.J.6
  • 32
    • 0031025358 scopus 로고    scopus 로고
    • A unified total synthesis of the immunomodulators (-)-rapamycin and (-)-27-demethoxyrapamycin: Assembly of the common C(1-20) perimeter and final elaboration
    • (b) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. J., Jr. A Unified Total Synthesis of the Immunomodulators (-)-Rapamycin and (-)-27-Demethoxyrapamycin: Assembly of the Common C(1-20) Perimeter and Final Elaboration. J. Am. Chem. Soc. 1997, 119, 962-973.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 962-973
    • Smith III, A.B.1    Condon, S.M.2    McCauley, J.A.3    Leazer Jr., J.L.4    Leahy, J.W.5    Maleczka Jr., R.J.6
  • 33
    • 0025160288 scopus 로고
    • Discodermolide: A new bioactive polyhydroxylated lactone from the marine sponge discodermia dissolute
    • Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discodermolide: A New Bioactive Polyhydroxylated Lactone from the Marine Sponge Discodermia dissolute. J. Org. Chem. 1990, 55, 4912-4915.
    • (1990) J. Org. Chem. , vol.55 , pp. 4912-4915
    • Gunasekera, S.P.1    Gunasekera, M.2    Longley, R.E.3    Schulte, G.K.4
  • 35
    • 35448991792 scopus 로고    scopus 로고
    • Emerging microtubule stabilizing agents for cancer chemotherapy
    • Discodermolide, subsequently shown to be a potent antitumor agent, is now in Phase I clinical trials (see: Myles, D. C. Emerging Microtubule Stabilizing Agents for Cancer Chemotherapy, Annu. Rep. Med. Chem., 2002, 37, 125-131.) and has led us to develop a highly efficient gram scale synthesis of the natural antipode.
    • (2002) Annu. Rep. Med. Chem. , vol.37 , pp. 125-131
    • Myles, D.C.1
  • 39
    • 2942692494 scopus 로고    scopus 로고
    • note
    • Williams described the first use of HMPA as an additive for the lithiation of dithianes; see ref 27. Best conditions for lithiation entail dropwise addition of t-BuLi to a solution of the dithiane in THF/HMPA (5-10% v/v) at -78 °C, followed by gradual warming to -45 °C over 30 min.
  • 40
    • 0021149831 scopus 로고
    • Total synthesis of (+)-phyllanthocin
    • Williams, D. R.; Sit, S.-Y. Total Synthesis of (+)-Phyllanthocin. J. Am. Chem. Soc. 1984, 106, 2949-2954.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 2949-2954
    • Williams, D.R.1    Sit, S.-Y.2
  • 41
    • 0028338336 scopus 로고
    • Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic
    • Smith, A. B., III; Chen, K.; Robinson, D. J.; Laasko, L. M.; Hale, K. J. Formal Total Synthesis of FK506. Concise Construction of the C(10)-C(34) Segment via an Effective Coupling Tactic. Tetrahedron Lett. 1994, 35, 4271-4274.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4271-4274
    • Smith III, A.B.1    Chen, K.2    Robinson, D.J.3    Laasko, L.M.4    Hale, K.J.5
  • 42
    • 2942666626 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Pennsylvania, Philadelphia, PA
    • Laasko, L. M. Ph.D. Thesis, University of Pennsylvania, Philadelphia, PA, 2001.
    • (2001)
    • Laasko, L.M.1
  • 43
    • 0022551475 scopus 로고
    • Bioactive marine metabolites. Part 16. Calyculin A. A novel antitumor metabolite from the marine sponge discodermia calyx
    • Kato Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K.; Fujita, S.; Furuya, T. Bioactive Marine Metabolites. Part 16. Calyculin A. A novel Antitumor Metabolite from the Marine Sponge Discodermia calyx. J. Am. Chem. Soc. 1986, 108, 2780-2781.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 2780-2781
    • Kato, Y.1    Fusetani, N.2    Matsunaga, S.3    Hashimoto, K.4    Fujita, S.5    Furuya, T.6
  • 45
    • 0033579151 scopus 로고    scopus 로고
    • Total synthesis of (+)-calyculin A and (-)-calyculin B: Cyanotetraene construction, asymmetric synthesis of the C(26-37) oxazole, fragment assembly, and final elaboration
    • (b) Smith, A. B., III; Friestad, G. K.; Barbosa, J.; Bertounesque, E.; Duan, J. J.-W.; Hull, K. G.; Iwashima, M.; Qui, Y.; Spoors, G.; Salvatore, B. A. Total Synthesis of (+)-Calyculin A and (-)-Calyculin B: Cyanotetraene Construction, Asymmetric Synthesis of the C(26-37) Oxazole, Fragment Assembly, and Final Elaboration. J. Am. Chem. Soc. 1999, 121, 10478-10486.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10478-10486
    • Smith III, A.B.1    Friestad, G.K.2    Barbosa, J.3    Bertounesque, E.4    Duan, J.J.-W.5    Hull, K.G.6    Iwashima, M.7    Qui, Y.8    Spoors, G.9    Salvatore, B.A.10
  • 47
    • 84986360437 scopus 로고
    • 13C-Labeled sulfur- and selenium-substituted organolithium derivatives
    • and references therein
    • 13C-Labeled Sulfur- and Selenium-Substituted Organolithium Derivatives. Helv. Chim. Acta 1984, 67, 1083-1099 and references therein.
    • (1984) Helv. Chim. Acta , vol.67 , pp. 1083-1099
    • Seebach, D.1    Gabriel, J.2    Häsig, R.3
  • 48
    • 33748939157 scopus 로고
    • The formation and stability of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane
    • (a) Beesely, R. M.; Ingold, C. K.; Thorpe, J. F. The formation and stability of spiro-Compounds. Part I. spiro-Compounds from cyclo-Hexane. J. Chem. Soc. 1915, 107, 1080-1105.
    • (1915) J. Chem. Soc. , vol.107 , pp. 1080-1105
    • Beesely, R.M.1    Ingold, C.K.2    Thorpe, J.F.3
  • 49
    • 0033011059 scopus 로고    scopus 로고
    • New gem- and vic-disubstituent effects on cyclizations
    • (b) Jung, M. E. New Gem- and Vic-Disubstituent Effects on Cyclizations. Synlett 1999, 843-846.
    • (1999) Synlett , pp. 843-846
    • Jung, M.E.1
  • 52
    • 84988058001 scopus 로고
    • 2-symmetrical enantiopure 1,5-Diols and β,β′-Dihydroxyketones as well as of enantiopure 1,3,5-Triols
    • 2-Symmetrical Enantiopure 1,5-Diols and β,β′-Dihydroxyketones as well as of Enantiopure 1,3,5-Triols. Synlett 1994, 511-512.
    • (1994) Synlett , pp. 511-512
    • Tietze, L.F.1    Geissler, H.2    Gewert, J.A.3    Hakobi, U.4
  • 53
    • 0001571904 scopus 로고
    • Two-directional chain synthesis and terminus differentiation
    • Schreiber, S. L. Two-directional Chain Synthesis and Terminus Differentiation. Chem. Ser. 1987, 27, 563-566.
    • (1987) Chem. Ser. , vol.27 , pp. 563-566
    • Schreiber, S.L.1
  • 54
    • 0002237394 scopus 로고
    • Some molecular-rearrangements of organosilicon compounds
    • Brook, A. G. Some Molecular-Rearrangements of Organosilicon Compounds. Acc. Chem. Res. 1974, 7, 77-84.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 77-84
    • Brook, A.G.1
  • 55
    • 0030030939 scopus 로고    scopus 로고
    • tert-butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1,3-rearrangement and 1,4-rearrangement of silyl group from carbon to oxide
    • An elegant study by Utimoto and co-workers demonstrated that solvent effects can be used to control the occurrence of silyl migrations: (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. tert- Butyldimethylsilyldihalomethyllithium as a Dihalomethylene Dianion Synthon. 1,3-Rearrangement and 1,4-Rearrangement of Silyl group from Carbon to Oxide. Tetrahedron 1996, 52, 503-514.
    • (1996) Tetrahedron , vol.52 , pp. 503-514
    • Shinokubo, H.1    Miura, K.2    Oshima, K.3    Utimoto, K.4
  • 56
    • 0027471608 scopus 로고
    • tert-Butyldimethylsilyldichloromethyllithium as a dichloromethylene dianion synthon. 1,3-Rearrangement of silyl group from carbon to oxide
    • (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. tert-Butyldimethylsilyldichloromethyllithium as a Dichloromethylene Dianion Synthon. 1,3-Rearrangement of Silyl Group from Carbon to Oxide. Tetrahedron Lett. 1993, 34, 1951-1954.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1951-1954
    • Shinokubo, H.1    Miura, K.2    Oshima, K.3    Utimoto, K.4
  • 57
    • 0030812082 scopus 로고    scopus 로고
    • Multicomponent linchpin couplings of silyl dithianes via solvent-controlled brook rearrangement
    • Smith, A. B., III; Boldi, A. M. Multicomponent Linchpin Couplings of Silyl Dithianes via Solvent-Controlled Brook Rearrangement. J. Am. Chem. Soc. 1997, 119, 6925-6926.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 6925-6926
    • Smith III, A.B.1    Boldi, A.M.2
  • 58
    • 0344443340 scopus 로고    scopus 로고
    • Multicomponent linchpin couplings. Reaction of dithiane anions with terminal epoxides, epichlorohydrin and vinyl epoxides: Efficient, rapid and stereocontrolled assembly of advanced fragments for complex molecule synthesis
    • Smith, A. B., III; Pitram, S. M.; Boldi, A. M.; Gaunt, M. J.; Sfouggatakis, C.; Moser, W. H. Multicomponent Linchpin Couplings. Reaction of Dithiane Anions with Terminal Epoxides, Epichlorohydrin and Vinyl Epoxides: Efficient, Rapid and Stereocontrolled Assembly of Advanced Fragments for Complex Molecule Synthesis. J. Am. Chem. Soc. 2003, 125, 14435-14445.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14435-14445
    • Smith III, A.B.1    Pitram, S.M.2    Boldi, A.M.3    Gaunt, M.J.4    Sfouggatakis, C.5    Moser, W.H.6
  • 59
    • 2942642844 scopus 로고    scopus 로고
    • note
    • Work in our laboratories has demonstrated that the observed silyl migration is intramolecular; see ref 48.
  • 61
    • 0027171060 scopus 로고
    • Isolation and structure of the remarkable human cancer cell-growth inhibitors spongistatin-2 and spongistatin-3 from an easter Indian ocean-spongia SP
    • (b) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. Isolation and Structure of the remarkable human cancer Cell-Growth Inhibitors Spongistatin-2 and Spongistatin-3 from an Easter Indian Ocean-Spongia SP. J. Chem. Soc., Chem. Commun. 1993, 1166-1168.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 1166-1168
    • Pettit, G.R.1    Cichacz, Z.A.2    Gao, F.3    Herald, C.L.4    Boyd, M.R.5
  • 63
    • 0035825173 scopus 로고    scopus 로고
    • The spongistatins: Architecturally complex natural products-part two: Synthesis of the C(29-51) subunit, fragment assembly and final elaboration of (+)-spongistatin 2
    • (b) Smith, A. B., III; Lin, Q. Y.; Doughty, V. A.; Zhuang, L. H.; McBriar, M. D.; Kerns, J. K.; Brook, C. S.; Murase, N.; Nakayama, K. The Spongistatins: Architecturally Complex Natural Products-Part Two: Synthesis of the C(29-51) Subunit, Fragment Assembly and Final Elaboration of (+)-Spongistatin 2. Angew. Chem., Int. Ed. 2001, 40, 196-199.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 196-199
    • Smith III, A.B.1    Lin, Q.Y.2    Doughty, V.A.3    Zhuang, L.H.4    McBriar, M.D.5    Kerns, J.K.6    Brook, C.S.7    Murase, N.8    Nakayama, K.9
  • 64
    • 0037529202 scopus 로고    scopus 로고
    • Total synthesis of (+)-spongistatin 1. An effective second-generation construction of an advanced EF wittig salt, fragment union and final elaboration
    • (c) Smith, A. B., III; Zhu, W.; Shirakami, S.; Sfouggatakis, C.; Doughty, V. A.; Bennet, C. S.; Sakamoto, Y. Total Synthesis of (+)-Spongistatin 1. An Effective Second-Generation Construction of an Advanced EF Wittig Salt, Fragment Union and Final Elaboration. Org Lett. 2003, 5, 761-764.
    • (2003) Org Lett. , vol.5 , pp. 761-764
    • Smith III, A.B.1    Zhu, W.2    Shirakami, S.3    Sfouggatakis, C.4    Doughty, V.A.5    Bennet, C.S.6    Sakamoto, Y.7
  • 65
    • 0037035004 scopus 로고    scopus 로고
    • Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate
    • Smith, A. B., III; Doughty, V. A.; Sfouggatakis, C.; Bennett, C. S.; Koyanagi, J.; Takeuchi, M. Spongistatin Synthetic Studies. An Efficient, Second-Generation Construction of an Advanced ABCD Intermediate. Org. Lett. 2002, 4, 783-786.
    • (2002) Org. Lett. , vol.4 , pp. 783-786
    • Smith III, A.B.1    Doughty, V.A.2    Sfouggatakis, C.3    Bennett, C.S.4    Koyanagi, J.5    Takeuchi, M.6
  • 66
    • 0023472148 scopus 로고
    • Stereochemical studies of the skipped-polyol polyene macrolide class: Degradation and partial structure determination of mycoticin A and B
    • and references therein
    • Schreiber, S. L.; Goulet, M. T. Stereochemical Studies of the Skipped-Polyol Polyene Macrolide Class: Degradation and Partial Structure Determination of Mycoticin A and B. Tetrahedron Lett. 1987, 28, 6001-6004 and references therein.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6001-6004
    • Schreiber, S.L.1    Goulet, M.T.2
  • 67
    • 0033576439 scopus 로고    scopus 로고
    • Multicomponent linchpin couplings of silyl dithianes: Synthesis of the schreiber C(16-28) trisacetonide subtarget for mycoticins A and B
    • Smith, A. B., III; Pitram, S. M. Multicomponent Linchpin Couplings of Silyl Dithianes: Synthesis of the Schreiber C(16-28) Trisacetonide Subtarget for Mycoticins A and B. Org. Lett. 1999, 1, 2001-2004.
    • (1999) Org. Lett. , vol.1 , pp. 2001-2004
    • Smith III, A.B.1    Pitram, S.M.2
  • 68
    • 0027159043 scopus 로고
    • Two-directional chain synthesis: An application to the synthesis of (+)-mycoticin A
    • Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. Two-Directional Chain Synthesis: an Application to the Synthesis of (+)-Mycoticin A. J. Am. Chem. Soc. 1993, 115, 3360-3361.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3360-3361
    • Poss, C.S.1    Rychnovsky, S.D.2    Schreiber, S.L.3
  • 71
    • 0013843444 scopus 로고
    • Rimocidin. I. Carbon skeleton, partial structure, and absolute configuration at C-27
    • (a) Cope, A. C.; Burrows, E. P.; Derieg, M. E.; Moon, S.; Wirth, W.-D. Rimocidin. I. Carbon Skeleton, Partial Structure, and Absolute Configuration at C-27. J. Org. Chem. 1965, 30, 5452-5460.
    • (1965) J. Org. Chem. , vol.30 , pp. 5452-5460
    • Cope, A.C.1    Burrows, E.P.2    Derieg, M.E.3    Moon, S.4    Wirth, W.-D.5
  • 73
    • 85065239587 scopus 로고
    • Selective sulphonylation with N-tosylimidazole. A one-step preparation of methyl 2,3-anhydro-4,6-o-benzylidene-α-d-mannopyranoside
    • Hicks, D. R.; Fraser-Reid, B. Selective Sulphonylation with N-Tosylimidazole. A One-Step Preparation of Methyl 2,3-Anhydro-4,6-O- benzylidene-α-D-mannopyranoside. Synthesis 1974, 203.
    • (1974) Synthesis , pp. 203
    • Hicks, D.R.1    Fraser-Reid, B.2
  • 74
    • 0141520339 scopus 로고    scopus 로고
    • (+)-Rimocidin synthetic studies. Construction of an advanced c(1-18) polyol fragment
    • Smith, A. B., III; Pitram, S. M.; Fuertes, M. J. (+)-Rimocidin Synthetic Studies. Construction of an Advanced C(1-18) Polyol Fragment. Org. Lett. 2003, 5, 2751-2754.
    • (2003) Org. Lett. , vol.5 , pp. 2751-2754
    • Smith III, A.B.1    Pitram, S.M.2    Fuertes, M.J.3
  • 76
    • 0001156916 scopus 로고
    • Cytotoxic metabolites of the marine sponge mycale adhaerens
    • Fusetani, N.; Sugawara, T.; Matsunaga, S.; Hirota, H. Cytotoxic Metabolites of the Marine Sponge Mycale adhaerens. J. Org. Chem. 1991, 56, 4971-4974.
    • (1991) J. Org. Chem. , vol.56 , pp. 4971-4974
    • Fusetani, N.1    Sugawara, T.2    Matsunaga, S.3    Hirota, H.4
  • 77
    • 0033592504 scopus 로고    scopus 로고
    • Synthesis of tedanolide and 13-deoxytedanolide. Assembly of a common C(1)-C(11) subtarget
    • Smith, A. B., III; Lodise, S. A. Synthesis of Tedanolide and 13-Deoxytedanolide. Assembly of a Common C(1)-C(11) Subtarget. Org. Lett. 1999, 1, 1249-1252.
    • (1999) Org. Lett. , vol.1 , pp. 1249-1252
    • Smith III, A.B.1    Lodise, S.A.2
  • 78
    • 2942649079 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Pennsylvania, Philadelphia, PA
    • Adams, C. M. Ph.D. Thesis, University of Pennsylvania, Philadelphia, PA, 2003.
    • (2003)
    • Adams, C.M.1
  • 79
    • 2942660271 scopus 로고    scopus 로고
    • note
    • While conversion of alcohols to the corresponding aldehydes or ketones is easily accomplished (e.g., Swern and Parikh-Doering oxidations), reliable conversion of an aldehyde to the corresponding acid, or derivative there of, in the presence of a dithiane is not well precedented.
  • 80
    • 0013590923 scopus 로고
    • Samarium-catalyzed intramolecular tishchenko reduction of β-hydroxy ketones. A stereoselective approach to the synthesis of differentiated anti 1,3-Diol monoesters
    • (a) Evans, D. A.; Hoveyda, A. H. Samarium-Catalyzed Intramolecular Tishchenko Reduction of β-Hydroxy Ketones. A Stereoselective Approach to the Synthesis of Differentiated Anti 1,3-Diol Monoesters. J. Am. Chem. Soc. 1990, 112, 6447-6449.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6447-6449
    • Evans, D.A.1    Hoveyda, A.H.2
  • 81
    • 0344789908 scopus 로고    scopus 로고
    • The tishchenko reaction and its modifications in organic synthesis
    • (b) Törmakangas, O. P., Koskinen, A. M. P. The Tishchenko reaction and its modifications in organic synthesis. Recent Res. Dev. Org. Chem. 2001, 5, 225-255.
    • (2001) Recent Res. Dev. Org. Chem. , vol.5 , pp. 225-255
    • Törmakangas, O.P.1    Koskinen, A.M.P.2
  • 82
    • 0001143623 scopus 로고
    • New preparations of lanthanide alkoxides and their catalytic activity in Meerwein-Ponndorf-Verley-Oppenauer reactions
    • (a) Namy, J. L.; Souppe, J.; Collin, J.; Kagan, H. B. New preparations of lanthanide alkoxides and their catalytic activity in Meerwein-Ponndorf-Verley- Oppenauer reactions. J. Org. Chem. 1984, 49, 2045-2049.
    • (1984) J. Org. Chem. , vol.49 , pp. 2045-2049
    • Namy, J.L.1    Souppe, J.2    Collin, J.3    Kagan, H.B.4
  • 83
    • 2142715741 scopus 로고    scopus 로고
    • Sequencing reactions with samarium(ii) iodide
    • (b) Molander, G. A.; Harris, C. R. Sequencing Reactions with Samarium(II) Iodide. Chem. Rev. 1996, 96, 307-338.
    • (1996) Chem. Rev. , vol.96 , pp. 307-338
    • Molander, G.A.1    Harris, C.R.2
  • 84
    • 0037069712 scopus 로고    scopus 로고
    • 2-promoted oxidation of aldehydes in the presence of electron-rich heteroatoms
    • 2-Promoted Oxidation of Aldehydes in the Presence of Electron-Rich Heteroatoms. Org. Lett. 2002, 4, 4539-4541.
    • (2002) Org. Lett. , vol.4 , pp. 4539-4541
    • Smith III, A.B.1    Lee, D.2    Adams, C.M.3    Kozlowski, M.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.