Journal
ORGANIC LETTERS
Volume 19, Issue 7, Pages 1922-1925Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00722
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Funding
- National Natural Science Foundation of China [21422203]
- National Young Top-notch Talent Support Program
- Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT)
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The first asymmetric total syntheses of scholarisine K and alstolactine A have ben accomplished. Our syntheses feature (1) ring closure metathesis and an intramolecular Heck reaction to construct the 1,3-bridged [3,3,1] bicycle (C-D ring), (2) intramolecular alkylation followed by Fischer indolization to forth the basic skeleton of akuammilines, and (3) bioinspired, acid-promoted epoxide opening/lactonization to generate the second lactone ring of alstolactine A. These results provide evidence of a biogenetic relationship between scholarisine K and alstolactine A, which,should facilitate the preparation of other akuammiline-type natural products and their derivatives for functional studies.
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