Flexible approach for the asymmetric synthesis of (−)-hyacinthacine A1 and its 7a-epimer

The diastereoselective nucleophilic addition of organic boronic ester to 3-hydroxy-2-substituted N-acyliminium ions 9 led to the formation of 2,5-cis-pyrrolidine 10, from which a convenient synthesis of (−)-7a-epi-1 was developed. In addition, an efficient asymmetric synthesis of (−)-hyacinthacine A...

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Bibliographic Details
Published inTetrahedron Vol. 70; no. 43; pp. 7936 - 7941
Main Authors Si, Chang-Mei, Mao, Zhuo-Ya, Ren, Rong-Guo, Du, Zhen-Ting, Wei, Bang-Guo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.10.2014
Elsevier
Subjects
Alkaloid
Asymmetric synthesis
Chemistry
Chemistry, Organic
Hyacinthacine
Lactam
Nucleophilic addition
Physical Sciences
Science & Technology
Hyacinthacine
Alkaloid
Asymmetric synthesis
Lactam
Nucleophilic addition
MARINE CYCLIC DEPSIPEPTIDE
GLUCOSIDASE INHIBITOR
PYRROLIZIDINE ALKALOIDS
AUSTRALINE
GLYCOSIDASE INHIBITORS
N,O-ACETAL
HYACINTHACINE A
POLYHYDROXYLATED PYRROLIDINE
NATURAL OCCURRENCE
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Summary:The diastereoselective nucleophilic addition of organic boronic ester to 3-hydroxy-2-substituted N-acyliminium ions 9 led to the formation of 2,5-cis-pyrrolidine 10, from which a convenient synthesis of (−)-7a-epi-1 was developed. In addition, an efficient asymmetric synthesis of (−)-hyacinthacine A1 1 was achieved through the reduction/ring-opening process. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.08.056