메뉴 건너뛰기




Volumn 51, Issue 3-4, 2011, Pages 329-345

From total synthesis to diverted total synthesis: Case studies in the amphidinolide series

Author keywords

catalysis; macrolides; metathesis; natural products; total synthesis

Indexed keywords


EID: 79953861207     PISSN: 00212148     EISSN: 18695868     Source Type: Journal    
DOI: 10.1002/ijch.201100006     Document Type: Review
Times cited : (72)

References (227)
  • 3
    • 33745714102 scopus 로고    scopus 로고
    • For attempted cloning of the polyketide synthase genes from amphidinolide producing algae and a discussion of their biosynthetic program, see the following and literature cited therein.
    • For attempted cloning of the polyketide synthase genes from amphidinolide producing algae and a discussion of their biosynthetic program, see the following and literature cited therein:, T. Kubota, Y. Iinuma, J. Kobayashi, Biol. Pharm. Bull. 2006, 29, 1314-1318.
    • (2006) Biol. Pharm. Bull. , vol.29 , pp. 1314-1318
    • Kubota, T.1    Iinuma, Y.2    Kobayashi, J.3
  • 9
    • 79953901587 scopus 로고    scopus 로고
    • Amphidinolide A
    • Amphidinolide A
  • 13
    • 79953880416 scopus 로고    scopus 로고
    • Presumed structure of amphidinolide A
    • Presumed structure of amphidinolide A
  • 18
    • 79953852492 scopus 로고    scopus 로고
    • Amphidinolide B series
    • Amphidinolide B series
  • 19
    • 79953881472 scopus 로고    scopus 로고
    • Ref.[10]
    • Ref.[10]
  • 21
    • 51349109146 scopus 로고    scopus 로고
    • correction: J. Am. Chem. Soc. 2008, 130, 11834
    • correction: J. Am. Chem. Soc. 2008, 130, 11834.
  • 22
    • 79953884251 scopus 로고    scopus 로고
    • Amphidinolide E
    • Amphidinolide E
  • 25
    • 33845491696 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 8019-8021
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8019-8021
  • 28
    • 33846594323 scopus 로고    scopus 로고
    • for 2-epi-amphidinolide E, see.
    • for 2-epi-amphidinolide E, see:, P. Va, W. R. Roush, Org. Lett. 2007, 9, 307-310.
    • (2007) Org. Lett. , vol.9 , pp. 307-310
    • Va, P.1    Roush, W.R.2
  • 31
    • 37349016936 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 9265-9270
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 9265-9270
  • 33
    • 79953891042 scopus 로고    scopus 로고
    • Amphidinolide J
    • Amphidinolide J
  • 36
    • 79953898920 scopus 로고    scopus 로고
    • Amphidinolide K
    • Amphidinolide K
  • 39
    • 70349783704 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 2364-2366.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2364-2366
  • 40
    • 79953879881 scopus 로고    scopus 로고
    • Iso-epoxy-Amphidinolide N and the closely related des-epoxy-caribenolide I
    • Iso-epoxy-Amphidinolide N and the closely related des-epoxy-caribenolide I
  • 43
    • 79953889964 scopus 로고    scopus 로고
    • Amphidinolide P
    • Amphidinolide P
  • 50
  • 59
    • 79953893512 scopus 로고    scopus 로고
    • Amphidinolide V
    • Amphidinolide V
  • 61
    • 34547235970 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5545-5548
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5545-5548
  • 63
    • 79953887500 scopus 로고    scopus 로고
    • Amphidinolide W
    • Amphidinolide W
  • 66
    • 79953853014 scopus 로고    scopus 로고
    • Amphidinolide X
    • Amphidinolide X
  • 68
    • 79953839053 scopus 로고    scopus 로고
    • Ref.[20a]
    • Ref.[20a]
  • 72
    • 70349918263 scopus 로고    scopus 로고
    • 19d.
    • 19d Angew. Chem. Int. Ed. 2009, 48, 5698-5700.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5698-5700
  • 73
    • 79953897827 scopus 로고    scopus 로고
    • Amphidinolide Y
    • Amphidinolide Y
  • 79
    • 77956034361 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 6032-6056
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6032-6056
  • 81
    • 78650111987 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 9592-9628.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9592-9628
  • 82
    • 79953854051 scopus 로고    scopus 로고
    • For other diverted total syntheses projects from our group modeled around cytotoxic macrolides, see
    • For other diverted total syntheses projects from our group modeled around cytotoxic macrolides, see
  • 94
  • 96
    • 22744448499 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4490-4527
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4490-4527
  • 99
    • 33749026617 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6086-6101.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 6086-6101
  • 109
    • 0037644400 scopus 로고    scopus 로고
    • For another advanced case, see.
    • For another advanced case, see:, A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817-2825.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2817-2825
    • Fürstner, A.1    Weintritt, H.2
  • 110
    • 0000172128 scopus 로고    scopus 로고
    • in (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, pp..
    • T. Ohkuma, R. Noyori, in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999, pp. 199-246.
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 1 , pp. 199-246
    • Ohkuma, T.1    Noyori, R.2
  • 121
    • 0035905656 scopus 로고    scopus 로고
    • For another instructive example, which shows the strong effect of a remote protecting group, see.
    • For another instructive example, which shows the strong effect of a remote protecting group, see:, A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286-5298.
    • (2001) Chem. Eur. J. , vol.7 , pp. 5286-5298
    • Fürstner, A.1    Dierkes, T.2    Thiel, O.R.3    Blanda, G.4
  • 132
    • 79953879087 scopus 로고    scopus 로고
    • The following studies were particularly suggestive
    • The following studies were particularly suggestive
  • 140
    • 4143108202 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3601-3605.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3601-3605
  • 147
    • 4644245555 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4704-4734
  • 148
    • 79953889453 scopus 로고    scopus 로고
    • Among others, the protocols described in the following publications were tested
    • Among others, the protocols described in the following publications were tested
  • 158
    • 79953860379 scopus 로고    scopus 로고
    • For applications, see: ref.[23d], ref.[74], and the following
    • For applications, see: ref.[23d], ref.[74], and the following
  • 168
  • 186
    • 79953888571 scopus 로고    scopus 로고
    • 2 lactone, cruentarene A)
    • 2 lactone, cruentarene A)
  • 190
    • 37349034615 scopus 로고    scopus 로고
    • Angew Chem. Int. Ed. 2007, 46, 9275-9278.
    • (2007) Angew Chem. Int. Ed. , vol.46 , pp. 9275-9278
  • 195
    • 0344012926 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5355-5357.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5355-5357
  • 198
  • 200
    • 34250824768 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3410-3449.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3410-3449
  • 205
    • 22744442306 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4442-4489
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4442-4489
  • 206
    • 0000397168 scopus 로고    scopus 로고
    • for a review on the alkyl-Suzuki reaction, see
    • for a review on the alkyl-Suzuki reaction, see:, S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701
    • (2001) Angew. Chem. , vol.113 , pp. 4676-4701
    • Chemler, S.R.1    Trauner, D.2    Danishefsky, S.J.3
  • 207
    • 0035905441 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4544-4568
  • 212
    • 20444381357 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3462-3466
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3462-3466
  • 224
    • 36549023143 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8707-8710
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8707-8710


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.