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Asymmetric Synthesis of (–)‐Lentiginosine by Double Aza‐Michael Reaction
Author(s) -
Liu SinWei,
Hsu HeChu,
Chang ChiaoHsin,
Tsai HuiHsu Gavin,
Hou DuenRen
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000691
Subject(s) - chemistry , michael reaction , adduct , metathesis , salt metathesis reaction , stereochemistry , organic chemistry , catalysis , polymerization , polymer
Total synthesis of (–)‐lentiginosine ( 1 ) was achieved in nine steps from (3 R ,4 R )‐3,4‐dihydroxy‐1,5‐hexadiene ( 2 ). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3‐oxonona‐1,4,8‐triene 6 , which was cyclised to 4‐oxopiperidine 7 by diastereoselective double aza‐Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2 R )‐4‐oxopiperidine 7 .
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