Total synthesis of cyclic diterpene tonantzitlolone based on a highly stereoselective substrate-controlled aldol reaction and ring-closing metathesis

Chemistry - A European Journal

Volumn 12, Issue 34, 2006, Pages 8719-8734

  Jasper, Christian ^a   Adibekian, Alexander ^b   Busch, Torsten ^c   Quitschalle, Monika ^c   Wittenberg, Rüdiger ^d   Kirschning, Andreas ^c  

^a UNIVERSITY OF BASEL   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^d DS Chemie GmbH   (Germany)

Author keywords

Aldol reactions; Natural products; Ring closing metathesis; Terpenes; Total synthesis

Indexed keywords

ALCOHOLS; ALDEHYDES; MOLECULAR STRUCTURE; REACTION KINETICS; SUBSTRATES; SYNTHESIS (CHEMICAL);

ALDOL REACTIONS; NATURAL PRODUCTS; RING CLOSING METATHESIS; TERPENES; TOTAL SYNTHESIS;

OLEFINS;

DITERPENE; MACROCYCLIC COMPOUND; TONANTZITLOLONE;

ARTICLE; CHEMICAL MODEL; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; DITERPENES; MACROCYCLIC COMPOUNDS; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 33845186923     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600082     Document Type: Article

References (63)

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59. It needs to be noted that the stereochemical outcome of the asymmetric dihydroxylation is reversed to the prediction given by the Sharpless mnemonic. Asymmetric induction with the commercially available dihydroxylation kit (AD-mix) did not result in any conversion. Dihydroxylation product 56a was only present in the open form, while diastereoisomer 56b was also present in the lactol form.™
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63. Lithium enolates tend to form dimers which may also prevent formation of transition states that involve coordination by the furan oxygen atom.