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Volumn 12, Issue 7, 2010, Pages 1556-1559

A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; PHOSPHATE; TETRAHYDROLIPSTATIN;

EID: 77950240183     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/0l1002913     Document Type: Article
Times cited : (39)

References (74)
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    • Diene diol (S,S)-8 can be synmesized from the corresponding l,5-dichloropentane-2,4-diol (Rychnovsky diol) in one step (see ref 6). For synthesis of the Rychnovsky diol, see
    • (a) Diene diol (S,S)-8 can be synmesized from the corresponding l,5-dichloropentane-2,4-diol (Rychnovsky diol) in one step (see ref 6). For synthesis of the Rychnovsky diol, see:
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    • S)-6, have been previously utilized for generation of the C1 - C14 and C15-C30 segments of dolabelide C, and gram-scale syntheses are now routinely carried out in our laboratory; see ref 10.
    • S)-6, have been previously utilized for generation of the C1 - C14 and C15-C30 segments of dolabelide C, and gram-scale syntheses are now routinely carried out in our laboratory; see ref 10.
  • 53
    • 84981828672 scopus 로고
    • R (see ref 6b). Workers at Chemical Abstracts Service kindly noted that Cahm - Ingold - Prelog priority rules dictate that "Contributions by d-orbitals to bonds of quadriligant atoms are neglected", and hence, the P=O in 6 should be treated as a P-O with assignment of least priority; see p 39.1 in. Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. 1966, 5, 385-415.
    • (1966) Angew. Chem., Int. Ed. , vol.5 , pp. 385-415
    • Cahn, R.S.1    Ingold, C.2    Prelog, V.3
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    • For CM/Wittig olefination, see
    • For Tandem metathesis/hydrogenation, see: (a) Louie, J.; Bielawski, C . W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313. For CM/Wittig olefination, see:
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  • 61
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    • For RCM/oxidation, see
    • (b) Murelli, R. P.; Snapper, M. L. Org. Lett. 2007, 9, 1749-1752. For RCM/oxidation, see:
    • (2007) Org. Lett. , vol.9 , pp. 1749-1752
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  • 63
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    • For tandem RCM/CM and hydrogenation, see
    • (d) Seigal, B. A.; Fajardo, C.; Snapper, M. L. J. Am. Chem. Soc. 2005, 127, 16329-16332. For tandem RCM/CM and hydrogenation, see:
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 16329-16332
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    • For CM/hydrogenation/cyclization, see
    • (h) Virolleaud, M-. A.; Piva, O. Tetrahedron Lett. 2007, 48, 1417-1420. For CM/hydrogenation/cyclization, see:
    • (2007) Tetrahedron Lett. , vol.48 , pp. 1417-1420
    • Virolleaud M-, A.1    Piva, O.2
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    • 2] sequence compared to sequential use of cat-B for the RCM and cat-C for the CM.
    • 2] sequence compared to sequential use of cat-B for the RCM. and cat-C for the CM.
  • 72
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.