Microwave-assisted intramolecular Diels-Alder reaction towards the total synthesis of symbioimine

Synlett

Volumn , Issue 18, 2008, Pages 2877-2881

  Born, Stephen ^a   Bacani, Genesis ^a   Olson, Erin E ^a   Kobayashi, Yoshihisa ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biomimetic reaction; Intramolecular Diels Alder reaction; Marine natural product; Microwave assisted reaction; Symbioimine

Indexed keywords

ALKALOID DERIVATIVE; SYMBIOIMINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG SYNTHESIS; ISOMERIZATION; MICROWAVE RADIATION; PRECURSOR; STEREOCHEMISTRY;

EID: 56849101963     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083501     Document Type: Article

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26. 2, -78°C.
27. Microwave instrument: CEM Discovery Labmate microwave system.
28. Microwave-assisted heating of 11 in ethanol provided the Diels-Alder adducts 12a and 12b in 69% with exo/endo = 1:2.
29. The minor diastereomer was assumed to be the exo-adduct. We do not exclude the possibility of epimerization of the major kinetic endo-adduct 14 to the minor exo-adduct under the reaction conditions.
30. As expected, the bulky dienophile below did not afford any Diels-Alder adduct even under the microwave-assisted heating conditions. The starting material was recovered quantitatively (Scheme 8).
31. 3): δ = 214.4, 160.8 (2 C), 147.6, 130.9, 129.8, 105.3 (2 C), 98.0, 55.2 (2 C), 50.2, 43.1, 38.5, 37.2, 32.1, 28.3, 24.8.