Premium
Diastereo‐ and Enantiocontrolled Synthesis of (–)‐Allosedamine via Cycloaddition of a Chiral Nitrone
Author(s) -
Oppolzer Wolfgang,
Deerberg Jörg,
Tamura Osamu
Publication year - 1994
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.19940770217
Subject(s) - chemistry , nitrone , cycloaddition , stereoselectivity , stereochemistry , organic chemistry , catalysis
The piperidine alkaloid (–)‐allosedamine ( 1 ) has been synthesized, in 21% overall yield, in nine steps starting from the formyl‐ester 4 . The synthesis features the reaction cascade 7 → 3 → 2 , involving asymmetric electrophilic enolate hydroxyamination, hydroxylamine/aldehyde condensation, and nitrone/styrene cycloaddition, as well as the reductive N/O cleavage‐decyanation 12 → 1 .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom