Journal
SYNLETT
Volume 31, Issue 18, Pages 1800-1804Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707283
Keywords
parvistemonine A; natural product; total synthesis; aza-Wittig reaction; Mitsunobu reaction
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Funding
- JSPS KAKENHI [JP16K08180, JP18K14876, JP19K06981]
- Pharmaceutical Society of Japan
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We have developed a concise diastereoselective total synthesis of (+/-)-parvistemonine A. By using a Mukaiyama-Michael addition, an aza-Wittig reaction, a Paal-Knorr pyrrole synthesis, an acid-mediated annulation, and a Mitsunobu reaction as key steps, we achieved a total synthesis in which the longest linear sequence was ten steps and the overall yield was 19.6%. Additionally, the relative stereochemistry of parvistemonine A was confirmed by X-ray crystallographic analysis for the first time.
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