A serendipitous synthesis of (+)-gregatin B, second structure revisions of the aspertetronins, gregatins, and graminin A, structure revision of the penicilliols

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2730-2733

  Burghart Stoll, Heike ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL CHLORIDE; ALLYL COMPOUND; FURAN DERIVATIVE; GRAMININ A; GREGATIN B; LACTONE; PENICILLIOL A; PENICILLIOL B;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; CYCLIZATION; FURANS; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79956081213     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2008318     Document Type: Article

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35. The enantiopurity of this compound was determined by HPLC (for details see Supporting Information).
36. 1H NMR comparisons in Scheme 4 yet our preparations of (-)-(S)- and (+)-(R)- 3a show that the descriptors "(+)" and "(S)" do not match for any enantiomer of 3a. The easiest way of reconciliating the findings of refs 13 and 14 with ours assumes that their 3a was (1) racemic [cf. our acid-catalyzed isomerization (-)-(S)- 2a ' rac-3a; Scheme 5 ] and (2) dextrorotatory because of an unnoticed impurity.
37. CCDC 813695 and 813696 contain the crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via the link www.ccdc.cam.ac.uk/data-request/cif.