. pi.-Facial selection in intermolecular Diels-Alder reactions: total syntheses of (+)-actinobolin and (+)-5, 6, 10-triepiactinobolin

AP Kozikowski, TR Nieduzak, T Konoike…

Index: Kozikowski; Nieduzak; Konoike; Springer Journal of the American Chemical Society, 1987 , vol. 109, # 17 p. 5167 - 5175

Full Text: HTML

Citation Number: 51

Abstract

Abstract: Syntheses of both 5, 6, 10-triepi-actinobolin and the antibiotic actinobolin are described in which a homochiral diene prepared from L-threonine is employed as a key component in a Diels-Alder reaction with an acetylenic dienophile. While the Diels-Alder reaction of this diene with methyl propiolate furnished the cycloadduct required for the synthesis of (+)-actinoblin as the minor diastereomer, the completion of the synthesis ...

Related Articles:

High yielding synthesis of dehydroamino acid and dehydropeptide derivatives

[Ferreira, Paula M.T.; Maia, Hernani L.S.; Monteiro, Luis S.; Sacramento, Joana Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 24 p. 3697 - 3703]

Synthetic studies on ezomycins: stereoselective route to a thymine octosyl nucleoside derivative

[Poon, Kevin W. C.; Lovell, Kimberly M.; Dresner, Kendra N.; Datta, Apurba Journal of Organic Chemistry, 2008 , vol. 73, # 2 p. 752 - 755]

Synthesis of acyclic nucleoside and nucleotide analogues from amino acids: a convenient approach to a PMEA–PMPA hybrid

[Tetrahedron, , vol. 56, # 29 p. 5077 - 5083]

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

[Journal of Organic Chemistry, , vol. 65, # 4 p. 1037 - 1049]

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

[Journal of Organic Chemistry, , vol. 65, # 4 p. 1037 - 1049]

More Articles...