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Volumn 71, Issue 20, 2006, Pages 7741-7746

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; HYDRATION; HYDROXYLATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33749126764     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061200h     Document Type: Article
Times cited : (28)

References (33)
  • 8
    • 0033576439 scopus 로고    scopus 로고
    • For formal syntheses and approaches toward mycoticin A, see: (b) Smith, A. B.; Pitram, S. M. Org. Lett. 1999, 1, 2001-2004.
    • (1999) Org. Lett. , vol.1 , pp. 2001-2004
    • Smith, A.B.1    Pitram, S.M.2
  • 10
    • 0001527822 scopus 로고
    • For background on oxo polyene macrolide antibiotics, see: Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
    • (1995) Chem. Rev. , vol.95 , pp. 2021-2040
    • Rychnovsky, S.D.1
  • 12
    • 33646074058 scopus 로고    scopus 로고
    • For recent approaches to γ-methyl-δ-hydroxyenoates, see: ref 4 and (a) Chen, Y.-H.; McDonald. F. E. J. Am. Chem. Soc. 2006, 128, 4568-4569.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4568-4569
    • Chen, Y.-H.1    McDonald, F.E.2
  • 24
    • 33749123562 scopus 로고    scopus 로고
    • note
    • Lower yields for the TBS series were due to minor loss of the TBS group in the carbonate-forming step.
  • 25
    • 33749137383 scopus 로고    scopus 로고
    • note
    • Carreira has prepared 19 by a three step sequence from 6d, see: ref 7a.
  • 26
    • 0028852540 scopus 로고
    • The regioselectivity of the asymmetric dihydroxylation of di- and trienoates has been studied by Sharpless and our group, see: (a) Berker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345.
    • (1995) Tetrahedron , vol.51 , pp. 1345
    • Berker, H.1    Soler, M.A.2    Sharpless, K.B.3
  • 28
    • 33749129861 scopus 로고    scopus 로고
    • note
    • This constitutes a reduction in the ratio of Pd versus phosphine to our optimized conditions for the des-methyl substrates but is in accordance with Tsuji's vinyl epoxide reduction, albeit with significantly lower catalyst loadings; see ref 6.
  • 29
    • 33749139397 scopus 로고    scopus 로고
    • note
    • HbHc = 2.4 Hz) for the proton at C-4, indicating the all-syn stereochemistry of both 14 and 15, see supporting information.
  • 30
    • 4444276636 scopus 로고    scopus 로고
    • note
    • It is noteworthy that the dihydroxylation of 16 appears to proceed with the opposite facial selectivity to the analogous (E,E)-diene, but this result is consistent with the Sharpless mnemonic; see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
  • 32
    • 33749118556 scopus 로고    scopus 로고
    • note
    • In general, the all-equatorial diastereomer 21 forms with even greater stereocontrol than 15.
  • 33
    • 33749124216 scopus 로고    scopus 로고
    • note
    • Presented in this Experimental Section are the general experimental procedures and spectral data for all new compounds. Complete experimental procedures and spectral data for all compounds are presented in Supporting Information.


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