Dramatic solvent effect on the diastereoselectivity of Michael addition: Study toward the synthesis of the ABC ring system of hexacyclinic acid

Organic Letters

Volumn 10, Issue 1, 2008, Pages 45-48

  Toueg, Julie ^a   Prunet, Joëlle ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; FUSED HETEROCYCLIC RINGS; HEXACYCLINIC ACID; MANGANESE; UNCLASSIFIED DRUG;

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

COPPER; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MANGANESE; MOLECULAR STRUCTURE; STEREOISOMERISM; STREPTOMYCES;

EID: 38349184575     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702566c     Document Type: Article

References (24)

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17. An inseparable mixture of ketone 8 and Michael acceptor 6a was obtained along with adducts 4a and 4′a, which prevented us from calculating a yield based on recovered starting material.
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21. When the reaction was carried out in nucleophilic solvents such as MeOH or EtOH, hemiketals of type 13 were formed, which partly explains the observed low yields.
22. Full conversion to alcohol 14 has not been optimized.
23. The stereochemistry of 14 was proven by NOESY experiments.
24. Calculation was run with ChemDraw 11.0 (CambrideSoft) using an MM2 force field.