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Total Synthesis of (−)‐Crinine. Use of Tandem Cationic Aza‐ Cope Rearrangement/ Mannich Cyclizations for the Synthesis of Enantiomerically Pure Amaryllidaceae Alkaloids
Author(s) -
Overman Larry E.,
Sugai Soji
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680324
Subject(s) - chemistry , cyclopentene , yield (engineering) , tandem , total synthesis , mannich reaction , cationic polymerization , stereochemistry , organic chemistry , catalysis , materials science , metallurgy , composite material
The total synthesis of enantiomerically pure (−)‐crinine ( 1 ) in 10 steps and 6% overall yield from cyclopentene oxide is reported. The key step was the rearrangement of 7 upon reaction with AgNO 3 at 25°C to give cis ‐perhydroindolone 8 in 81% yield.
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