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Volumn 130, Issue 52, 2008, Pages 17938-17954

Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach

Author keywords

[No Author keywords available]

Indexed keywords

ATOM ECONOMY; ECONOMIC APPROACH; ENANTIOSPECIFIC; NATURAL PRODUCTS; OXIDATION STATE; REDOX MANIPULATION; TOTAL SYNTHESIS;

EID: 58849128316     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806981k     Document Type: Article
Times cited : (246)

References (119)
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    • These locations include the Marshall Islands (ref 1), the Everglades in Florida (ref 2b), Australia (ref 2f), Micronesia (ref 2h), Papua New Guinea (ref 2i), and Israel (ref 2k).
    • These locations include the Marshall Islands (ref 1), the Everglades in Florida (ref 2b), Australia (ref 2f), Micronesia (ref 2h), Papua New Guinea (ref 2i), and Israel (ref 2k).
  • 38
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    • (d) López-Alvarado, P.; Garc?́a-Granda, S.; Álvarez-Rúa, C.; Avendaño, C. Eur. J. Org. Chem. 2002, 1702-1707.
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    • See the following texts, and references therein: a, Wiley-VCH: Weinheim
    • See the following texts, and references therein: (a) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; Wiley-VCH: Weinheim, 1996.
    • (1996) Classics in Total Synthesis
    • Nicolaou, K.C.1    Sorensen, E.J.2
  • 58
    • 67849116863 scopus 로고    scopus 로고
    • The retro-aldol reaction was the major competing pathway.
    • The retro-aldol reaction was the major competing pathway.
  • 76
    • 67849124307 scopus 로고    scopus 로고
    • Prolonged exposure to triflic acid led to product decomposition; therefore, the reaction was quenched early and the starting material was recycled
    • Prolonged exposure to triflic acid led to product decomposition; therefore, the reaction was quenched early and the starting material was recycled.
  • 97
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    • (d) Gung, B. W. Chem. Rev. 1999, 99, 1377-1386.
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    • Gung, B.W.1
  • 101
    • 67849106514 scopus 로고    scopus 로고
    • This alternate reaction pathway was also noted in Wender's studies
    • This alternate reaction pathway was also noted in Wender's studies.
  • 102
    • 67849084969 scopus 로고    scopus 로고
    • Alternative chlorination conditions were attempted (SOCl 2/base, PPh3/ CCl4, PPh3/ZnCl 2/DEAD, MsCl/Pyr, PPh3/Cl2, DMAP/CS(imid) 2, COCl)2, TCT, TMSCl/BiCl3) but were unsuccessful at providing the desired product, and retro-aldol product was observed on at least one occasion
    • 3) but were unsuccessful at providing the desired product, and retro-aldol product was observed on at least one occasion.
  • 103
    • 67849128674 scopus 로고    scopus 로고
    • In fact, the reactivity of 47 and downstream intermediates differed significantly from that observed with the 12-epi-fischerindole U series
    • In fact, the reactivity of 47 and downstream intermediates differed significantly from that observed with the 12-epi-fischerindole U series.
  • 104
    • 67849133332 scopus 로고    scopus 로고
    • Attempts to utilize microwave irradiation to promote this reaction led to dechlorination of the compound and were therefore not amenable for this series of chlorinated natural products
    • Attempts to utilize microwave irradiation to promote this reaction led to dechlorination of the compound and were therefore not amenable for this series of chlorinated natural products.
  • 107
    • 67849101808 scopus 로고    scopus 로고
    • Until this point, for initial studies into the synthesis of these natural products, (R)-carvone oxide was used because of its significantly lower cost.
    • Until this point, for initial studies into the synthesis of these natural products, (R)-carvone oxide was used because of its significantly lower cost.
  • 108
    • 67849116126 scopus 로고    scopus 로고
    • The same oxidants were utilized as for 10, as well as DMDO and DMP.
    • The same oxidants were utilized as for 10, as well as DMDO and DMP.
  • 109
    • 67849119559 scopus 로고    scopus 로고
    • From this point on, (S)-carvone oxide was utilized to allow access to the correct enantiomer of the natural product.
    • From this point on, (S)-carvone oxide was utilized to allow access to the correct enantiomer of the natural product.
  • 110
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    • It was assumed that the isonitrile might react disastrously with various oxidants; therefore, the formamide was utilized in these trials
    • It was assumed that the isonitrile might react disastrously with various oxidants; therefore, the formamide was utilized in these trials.
  • 111
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    • As determined by AM1 calculations.
    • As determined by AM1 calculations.
  • 113
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    • The Wood group recently reported that their attempts to convert 10-epi-78 into 12 were unsuccessful, utilizing a variety of conditions see ref 17b
    • The Wood group recently reported that their attempts to convert 10-epi-78 into 12 were unsuccessful, utilizing a variety of conditions (see ref 17b).
  • 116
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    • Trost, B. M. Science 1991, 254, 1471-1477.
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    • For illuminating discussions of oxidation state control in synthesis, see: a
    • For illuminating discussions of oxidation state control in synthesis, see: (a) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147-155.
    • (1974) Acc. Chem. Res , vol.7 , pp. 147-155
    • Evans, D.A.1    Andrews, G.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.