Dihydropyrones as dienophiles in the Diels-Alder reaction: Application to the synthesis of 1-oxadecalones

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1776-1777

  Chen, Deqi ^a   Wang, Junquan ^a   Totah, Nancy I ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 OXADECALONE DERIVATIVE; 2,3 DIHYDRO 4 PYRONE; 5 ACETYL 2,3 DIHYDRO 4 PYRONE; 5 CARBETHOXY 2,3 DIHYDRO 4 PYRONE; 5 CYANO 2,3 DIHYDRO 4 PYRONE; 5 PHENYLSULFONE 2,3 DIHYDRO 4 PYRONE; PHOMACTIN A; PYRONE DERIVATIVE; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; REACTION ANALYSIS; REDUCTION;

EID: 0033583017     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982488g     Document Type: Article

References (21)

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15. To date we have been unable to identify conditions under which the parent 2,3-dihydro-2,2-dimethyl-4-pyranone will react, even with highly activated dienes.
16. The stereochemistry of the major diastereomer is tentatively assigned as that bearing an α-methoxy function at C5 (cf. 6). This stereochemical assignment is based on the observation of long-range coupling between protons on C5 and C8a of the major Diels - Alder adduct.
17. Though 85% represents the yield of the purified Diels - Alder adduct, routinely these compounds are utilized in subsequent transformations without purification.
18. Ethyl p-hydroxybenzoate can be isolated cleanly from the reaction mixture.
19. Presumably, the presence of a substituent at C5 impedes hydration of the C4 ketone due to an increase in steric hindrance.
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