Asymmetric synthesis of epohelmins A, B and 3-epi ent-epohelmin A

An efficient method for asymmetric synthesis of epohelmins A (3), B (4) and their isomer 24 is detailed in this report. The key feature in this divergent synthesis includes the SmI2-induced cross-coupling of N-tert-butanesulfinyl imine 10 with chiral aldehyde 9 derived from d-malic acid. A cascade c...

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Bibliographic Details
Published inTetrahedron Vol. 72; no. 49; pp. 8091 - 8098
Main Authors Si, Chang-Mei, Liu, Yi-Wen, Mao, Zhuo-Ya, Han, Pan, Du, Zhen-Ting, Wei, Bang-Guo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.12.2016
Elsevier
Subjects
Asymmetric synthesis
Cascade cyclization
Chemistry
Chemistry, Organic
Cross-coupling
Epohelmins
Natural product
Physical Sciences
Science & Technology
Natural product
Epohelmins
Cross-coupling
Cascade cyclization
Asymmetric synthesis
ANALOGS
DIVERGENT SYNTHESIS
BETA-AMINO ALCOHOLS
SECONDARY ALCOHOLS
ACID-DERIVATIVES
TERT-BUTANESULFINYL IMINES
LANOSTEROL SYNTHASE INHIBITORS
CONSTRUCTION
OXA-MICHAEL REACTION
FUNGAL STRAIN FKI-0929
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Summary:An efficient method for asymmetric synthesis of epohelmins A (3), B (4) and their isomer 24 is detailed in this report. The key feature in this divergent synthesis includes the SmI2-induced cross-coupling of N-tert-butanesulfinyl imine 10 with chiral aldehyde 9 derived from d-malic acid. A cascade cyclization to the pyrrolizidine skeleton is achieved in our synthetic route for epohelmins. In addition, an interesting intramolecular oxa-Michael addition was observed for epohelmin A (3). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.10.047