Enantioselective total syntheses of (+)- and (-)-ottelione A and (+)- and (-)-ottelione B. Absolute configuration of the novel, biologically active natural products

Tetrahedron Letters

Volumn 44, Issue 35, 2003, Pages 6733-6736

  Mehta, Goverdhan ^a   Islam, Kabirul ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; CYCLOPENTADIENE DERIVATIVE; NATURAL PRODUCT; OTTELIONE A; OTTELIONE B; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY;

BETULACEAE;

EID: 0043172231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01643-5     Document Type: Article

References (20)

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12. 3). We are most grateful to Professor Hoye and Dr. Bouchard for information regarding the rotations of otteliones.
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15. 4.
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18. 8 >99% ee, with the literature values.
19. We greatly appreciate the free and helpful exchange of information with Professor Hoye that proved crucial in arriving at the correct absolute configuration of otteliones. Hoye's group has independently arrived at the same conclusion about the absolute configuration of otteliones on the basis of the Mosher ester studies with the alcohol derived from the reduction of ottelione A.
20. D -276 having high negative (opposite) rotation and thus leading to the observation of net negative rotation for ottelione A.