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Volumn 8, Issue 3, 2006, Pages 531-534

Total synthesis of apratoxin A

Author keywords

[No Author keywords available]

Indexed keywords

APRATOXIN A; DEPSIPEPTIDE; THIAZOLE DERIVATIVE;

EID: 32644444667     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052907d     Document Type: Article
Times cited : (90)

References (33)
  • 6
    • 32644450535 scopus 로고    scopus 로고
    • note
    • Total synthesis of apratoxin A has been presented in the 2nd Yamada Symposium on Key Natural Organic Molecules in Biological Systems, 2005, Hyogo, Japan.
  • 11
    • 32644454011 scopus 로고    scopus 로고
    • note
    • Forsyth reported that thiazoline formation from the thioester of the modified cysteine derivative could not avoid elimination of the adjacent hydroxy group corresponding to the C35 position.
  • 12
    • 20444411190 scopus 로고    scopus 로고
    • We attempted thioamide formation from N-Boc-Pro-Dtena(O-TBS)-moSer(O-TBS) -OAll using a Lawesson reagent. However, it failed because of Michael addition of the formed thioamide to the α,β-unsaturated ester. The similar result was also recently reported. Xu, Z.; Ye, T. Tetrahedron: Asymmetry 2005, 16, 1905-1912.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1905-1912
    • Xu, Z.1    Ye, T.2
  • 14
    • 0034750244 scopus 로고    scopus 로고
    • (b) List, B. Synlett 2001, 1675-1685.
    • (2001) Synlett , pp. 1675-1685
    • List, B.1
  • 17
    • 32644434337 scopus 로고    scopus 로고
    • note
    • The stereochemistry was determined by nOe observation after formation of lactone with the secondary alcohol.
  • 19
    • 32644451567 scopus 로고    scopus 로고
    • note
    • Forsyth did the aldol reaction after attachment with proline carboxylic acid. See ref 2.
  • 24
    • 12044258245 scopus 로고
    • HATU = O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate: Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1
  • 26
    • 0026498006 scopus 로고
    • Although other methods were evaluated for effecting this transformation, these proved problematic, (a) Walker, M. A.; Hearthcock, C. H. J. Org. Chem. 1992, 57, 5566-5568.
    • (1992) J. Org. Chem. , vol.57 , pp. 5566-5568
    • Walker, M.A.1    Hearthcock, C.H.2
  • 29
  • 30
    • 32644441803 scopus 로고    scopus 로고
    • note
    • The β-elimination of the O-Troc group was observed during silica gel column purification.
  • 31
    • 32644446375 scopus 로고    scopus 로고
    • note
    • 4OAc resulted in hydrolysis of the thiazoline ring.
  • 33
    • 32644434719 scopus 로고    scopus 로고
    • note
    • The use of morpholine instead of N-methylaniline cleaved the Fmoc group on the proline ring in 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.