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Volumn 350, Issue 18, 2008, Pages 2885-2891

An enantioselective synthesis of the ABD tricycle for (-)-phoinactin A featuring Rawal's asymmetric diels-alder cycloaddition

Author keywords

Asymmetric Diels Alder cycloaddition; Chromium(II) salen catalyst; Intramolecular oxa 3+3 annulation; Phomactin A; Rawal's 1 amino3 siloxy 1,3 butadiene

Indexed keywords


EID: 57849117425     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800552     Document Type: Article
Times cited : (28)

References (89)
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    • For total synthesis of (±)-phomactin A, see: a) W. P. D. Goldring, G. Pattenden, Chem. Commun. 2002, 1736;
    • For total synthesis of (±)-phomactin A, see: a) W. P. D. Goldring, G. Pattenden, Chem. Commun. 2002, 1736;
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    • For total synthesis of (+)-phomactin A, see : P. J. Mohr, R. L. Halcomb, J. Am. Chem. Soc. 2003, 125, 1712.
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    • For total synthesis of (±)-phomactin B2, see: J. Huang, C. Wu, W. D. Wulff, J. Am. Chem. Soc. 2007, 129, 13366.
    • For total synthesis of (±)-phomactin B2, see: J. Huang, C. Wu, W. D. Wulff, J. Am. Chem. Soc. 2007, 129, 13366.
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    • For applications in natural product syntheses, see; d
    • For applications in natural product syntheses, see; d) A. V. Kurdyumov, R. P. Hsung, J. Am. Chem. Soc. 2006, 128, 6272;
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    • See Supporting Information for procedures and characterizations of new compounds
    • See Supporting Information for procedures and characterizations of new compounds.
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    • PhD thesis;
    • b) Y. Huang, PhD thesis;
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    • S. A. Kozmin, V. H. Rawal, J. Am. Chem. Soc. 1998, #M20##124, 4628.
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    • For some recent applications and studies involving Rawal's diene, see: a
    • For some recent applications and studies involving Rawal's diene, see: a) A. Padwa, S. K. Bur, H. Zhang, J. Org. Chem. 2005, 70, 6833;
    • (2005) J. Org. Chem , vol.70 , pp. 6833
    • Padwa, A.1    Bur, S.K.2    Zhang, H.3
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    • The use of Danishefsky's diene and Corey's oxazaborolidine catalyst 12 only returned the related 1,4-addition product i and 1,2-addition product ii. a E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421;
    • The use of Danishefsky's diene and Corey's oxazaborolidine catalyst 12 only returned the related 1,4-addition product i and 1,2-addition product ii. a) E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421;
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    • c) for application of Cr(III)-salen catalysts in enantioselective hetero-DielsAlder reactions: S. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403.
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    • Only after deprotection of the TES ether, some chromatographic separation was observed which allowed us to attain a sufficiently pure sample to characterize the side product 27.
    • Only after deprotection of the TES ether, some chromatographic separation was observed which allowed us to attain a sufficiently pure sample to characterize the side product 27.
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    • Also isolated was a 25% yield of the two wrong tricycles iiia and iiib as an inseparable 4:1 atropisomeric mixture see ref.[11
    • [11]).


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