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Volumn 42, Issue 33, 2003, Pages 3934-3938

Formal synthesis of Leucascandrolide A

Author keywords

Allylation; Antitumor agents; Asymmetric synthesis; Macrolide; Natural products

Indexed keywords

HYDRIDES; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 0042819672     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351817     Document Type: Article
Times cited : (52)

References (39)
  • 9
    • 85047700139 scopus 로고    scopus 로고
    • b) A. Fettes, E. M. Carreira, Angew. Chem. 2002, 114, 4272; Angew. Chem. Int. Ed. 2002, 41, 4098;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4098
  • 12
    • 0037455379 scopus 로고    scopus 로고
    • d) I. Paterson, M. Tudge, Angew. Chem. 2003, 115, 357; Angew. Chem. Int. Ed. 2003, 42, 343.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 343
  • 15
    • 84982061441 scopus 로고
    • The synthesis of the epoxide 5 proceeds through the alkylation of 2-lithio-1,3-dithiane with (R)-epichlorohydrin (97% ee, Aldrich): a) M. Braun, D. Seebach, Chem. Ber. 1976, 109, 669; b) D. Seebach, I. Willert, A. Beck, B. T. Groebel, Helv. Chim. Acta 1978, 61, 2510.
    • (1976) Chem. Ber. , vol.109 , pp. 669
    • Braun, M.1    Seebach, D.2
  • 16
    • 0001378955 scopus 로고
    • The synthesis of the epoxide 5 proceeds through the alkylation of 2-lithio-1,3-dithiane with (R)-epichlorohydrin (97% ee, Aldrich): a) M. Braun, D. Seebach, Chem. Ber. 1976, 109, 669; b) D. Seebach, I. Willert, A. Beck, B. T. Groebel, Helv. Chim. Acta 1978, 61, 2510.
    • (1978) Helv. Chim. Acta , vol.61 , pp. 2510
    • Seebach, D.1    Willert, I.2    Beck, A.3    Groebel, B.T.4
  • 20
    • 84989478646 scopus 로고
    • The synthesis of the aldehyde 8 proceeds by the mono-pmethoxybenzylation of 1,3-propanediol followed by Swern oxidation: A. J. Mancuso, D. Swern, Synthesis 1981, 165.
    • (1981) Synthesis , pp. 165
    • Mancuso, A.J.1    Swern, D.2
  • 23
    • 0038499149 scopus 로고
    • The bromide 10 is available from the corresponding homoallylic alcohol by tosylation (TsCl, D MAP, pyridine; 98%), followed by exchange with lithium bromide (DME 50°C; 65%). For the synthesis of the starting homoallylic alcohol, see: J. D. White, G. N. Reddy, G. O. Spessard, J. Am. Chem. Soc. 1988, 110, 1624.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1624
    • White, J.D.1    Reddy, G.N.2    Spessard, G.O.3
  • 24
    • 0041936119 scopus 로고    scopus 로고
    • note
    • The epoxide 11 is available from D-malic acid in four steps. (equation presented)
  • 27
    • 0042937801 scopus 로고    scopus 로고
    • note
    • A complete study of matched and mismatched elements of stereochemistry will be detailed in further reports devoted to the asymmetric-allylation process.
  • 33
    • 0042937800 scopus 로고    scopus 로고
    • note
    • Either of the diastereomeric alcohols (R or S at C17) could potentially be a valuable intermediate toward lactone 2, depending on the strategy chosen: macrocyclization with retention of configuration at C17 (Yamaguchi protocol) or Mitsunobu macrocyclization with inversion of configuration at C17. For example, compare the reports of references [4a] and [5b].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.