Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 10, Pages 2354-2359Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201705575
Keywords
enantiospecific; diastereospecific; indole alkaloids; Pictet-Spengler reaction; total synthesis
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Funding
- NIH [NS076517, MH096463]
- American Society for Engineering Education (ASEE)
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Extension of the asymmetric Pictet-Spengler reaction to bulkier N-b-alkylated tryptophan derivatives resulted in an improved stereospecific access to the key bicyclo[3.3.1]nonane core of bioactive C-19 methyl substituted sarpagine/macroline/ajmaline indole alkaloids with excellent diastereoselectivity by internal asymmetric induction. Complete stereocontrol of the C-19 methyl function in either the alpha- or beta-configuration was achieved, which enables the total synthesis of any member from this group of thirty alkaloids. We report herein, the total synthesis of macrocarpines (A-C) 1-3, talcarpine 4, N(4)-methyl-N(4),21-secotalpinine 5, dihydroperaksine 8 and deoxyperaksine 9.
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