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Volumn 54, Issue 21, 2015, Pages 6241-6245

Selective formation of a trisubstituted alkene motif by trans-Hydrostannation/Stille coupling: Application to the total synthesis and late-Stage modification of 5,6-Dihydrocineromycin B

Author keywords

alkyne metathesis; cross coupling; hydrostannation; natural products; ruthenium

Indexed keywords

ANTIBIOTICS; CATALYSIS; CHEMICAL REACTIONS; HYDROCARBONS; KETONES; RUTHENIUM;

EID: 84928999151     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501608     Document Type: Article
Times cited : (63)

References (115)
  • 12
    • 33749026730 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 5194-5254.
    • (2006) Angew. Chem. , vol.118 , pp. 5194-5254
  • 13
    • 0014588868 scopus 로고
    • Moreover, Ref. [5] suggests that 1 interferes with the peptidoglycan biosynthesis, a mode of action that is unprecedented for 14-membered macrolides; earlier studies had proposed inhibition of the nicotinate biosynthesis, see.
    • Moreover, Ref. [5] suggests that 1 interferes with the peptidoglycan biosynthesis, a mode of action that is unprecedented for 14-membered macrolides; earlier studies had proposed inhibition of the nicotinate biosynthesis, see, F. Reusser, J. Bacteriol. 1969, 100, 11-13.
    • (1969) J. Bacteriol. , vol.100 , pp. 11-13
    • Reusser, F.1
  • 21
    • 17144389818 scopus 로고    scopus 로고
    • Angew. Chem. 2001, 113, 925-927.
    • (2001) Angew. Chem. , vol.113 , pp. 925-927
  • 25
    • 79953851949 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 6168-6193
    • (2010) Angew. Chem. , vol.122 , pp. 6168-6193
  • 27
    • 79953881471 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 9786-9823
    • (2010) Angew. Chem. , vol.122 , pp. 9786-9823
  • 30
    • 85028226042 scopus 로고    scopus 로고
    • Although the RCM product was the correct isomer, it is emphasized that RCM is substrate-controlled; catalysts able to enforce the formation of E-configured trisubstituted olefins are currently unknown. For general discussions, see
    • Although the RCM product was the correct isomer, it is emphasized that RCM is substrate-controlled; catalysts able to enforce the formation of E-configured trisubstituted olefins are currently unknown. For general discussions, see
  • 31
    • 84889847822 scopus 로고    scopus 로고
    • (UNSP 1229713)
    • A. Fürstner, Science 2013, 341, 1357 (UNSP 1229713)
    • (2013) Science , vol.341 , pp. 1357
    • Fürstner, A.1
  • 33
    • 85028202419 scopus 로고    scopus 로고
    • The difficulties in forming trisubstituted alkenes flanked by an -OR group by RCM and the potential lack of control over the olefin geometry is by no means a specific problem of 3; for other instructive cases, see
    • The difficulties in forming trisubstituted alkenes flanked by an -OR group by RCM and the potential lack of control over the olefin geometry is by no means a specific problem of 3; for other instructive cases, see
  • 37
    • 84878244133 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 2860-2887.
    • (2013) Angew. Chem. , vol.125 , pp. 2860-2887
  • 39
    • 0000775011 scopus 로고    scopus 로고
    • Angew. Chem. 1998, 110, 1758-1760
    • (1998) Angew. Chem. , vol.110 , pp. 1758-1760
  • 42
    • 84905746595 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 3700-3704.
    • (2014) Angew. Chem. , vol.126 , pp. 3700-3704
  • 43
    • 85028203308 scopus 로고    scopus 로고
    • See also
    • See also
  • 45
    • 84897465104 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 14300-14304
    • (2013) Angew. Chem. , vol.125 , pp. 14300-14304
  • 47
    • 84872288304 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 373-378
    • (2013) Angew. Chem. , vol.125 , pp. 373-378
  • 49
    • 84920484909 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 8728-8740.
    • (2014) Angew. Chem. , vol.126 , pp. 8728-8740
  • 55
    • 84863674022 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 11575-11579.
    • (2011) Angew. Chem. , vol.123 , pp. 11575-11579
  • 57
    • 84929005597 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 4050-4054
    • (2015) Angew. Chem. , vol.127 , pp. 4050-4054
  • 64
    • 79251560239 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 6301-6304.
    • (2010) Angew. Chem. , vol.122 , pp. 6301-6304
  • 72
    • 84871102318 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 7035-7039
    • (2012) Angew. Chem. , vol.124 , pp. 7035-7039
  • 74
    • 81755165038 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 8898-8903
    • (2011) Angew. Chem. , vol.123 , pp. 8898-8903
  • 77
    • 85028221156 scopus 로고    scopus 로고
    • An in-depth discussion will be the subject of a forthcoming publication from our group.
    • An in-depth discussion will be the subject of a forthcoming publication from our group.
  • 79
    • 85028197721 scopus 로고    scopus 로고
    • In contrast, Stille-type reactions with higher alkyl halides are more common; for leading references see the following and literature cited therein
    • In contrast, Stille-type reactions with higher alkyl halides are more common; for leading references see the following and literature cited therein
  • 81
    • 0346124463 scopus 로고    scopus 로고
    • Angew. Chem. 2003, 115, 5233-5236
    • (2003) Angew. Chem. , vol.115 , pp. 5233-5236
  • 95
    • 85028206461 scopus 로고    scopus 로고
    • For applications, see
    • For applications, see
  • 98
    • 79953842569 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 318-323
    • (2011) Angew. Chem. , vol.123 , pp. 318-323
  • 108
    • 84922025382 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 1953-1956.
    • (2015) Angew. Chem. , vol.127 , pp. 1953-1956
  • 111
    • 85028199237 scopus 로고    scopus 로고
    • D value of analytically pure synthetic 3 and that of the natural sample has already been noted before, see Ref. [13].
    • D value of analytically pure synthetic 3 and that of the natural sample has already been noted before, see Ref. [13].
  • 112
    • 0343874512 scopus 로고
    • in (Eds.: A. R. Rees, O. Katritzky, C. W. Meth-Cohn), Elsevier Science, Oxford, .
    • A. C. Regan, in Comprehensive Functional Group Transformations, Vol. 1 (Eds.:, A. R. Rees, O. Katritzky, C. W. Meth-Cohn,), Elsevier Science, Oxford, 1995, pp. 501-551.
    • (1995) Comprehensive Functional Group Transformations, Vol. 1 , pp. 501-551
    • Regan, A.C.1
  • 115
    • 85028225700 scopus 로고    scopus 로고
    • CCDC 1048778 (20) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 1048778 (20) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.